ChemicalBook CAS DataBase List 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl synthesis

6synthesis methods

Product Name:2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
CAS Number:657408-07-6
Molecular formula:C26H35O2P
Molecular Weight:410.53

694-80-4 Synthesis

694-80-4
392 suppliers
$5.00/10g

151-10-0
447 suppliers
$5.00/10g

16523-54-9 Synthesis

16523-54-9
265 suppliers
$8.00/1g

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

657408-07-6
335 suppliers
$6.00/1g

Yield:657408-07-6 36%

Reaction Conditions:

Stage #1: 1,3-Dimethoxybenzenewith n-butyllithium in tetrahydrofuran at 0 - 20; for 3.5 h;
Stage #2: 2-bromo-1-chlorobenzene in tetrahydrofuran at 0; for 0.5 h;
Stage #3: chlorodicyclohexylphosphane

Steps:

To a solution of 1,3-dimethoxybenzene (2 ml, 15.30 mmol) in anhydrous THF (35 ml) at 0° C., nBuLi (6.2 ml, 15.50 mmol) is added to the dropping funnel for 5 min. The reaction medium is stirred at room temperature for 3.5 h, then 2-bromochlorobenzene (1.6 ml, 13.70 mmol) is added by syringe, dropwise, at 0° C., for 30 min. After 15 min of stirring, the reaction medium is cooled to -78° C. and nBuLi (6.20 ml, 15.50 mmol) is added to the dropping funnel dropwise for 5 min. After 30 min, chlorodicyclohexylphosphine (3.03 ml, 13.70 mmol) is added. The reaction medium is maintained at -78° C. for 1 h, under rapid stirring (mechanical stirring). After returning to room temperature, the precipitate obtained is filtered on a fritted disc containing silica topped with a layer of cellulose acetate, with 600 ml ethyl acetate. The solvents are evaporated with a rotary evaporator, and the orange oil obtained is recrystallized in acetone to obtain S-Phos ligand in the form of white crystals with a yield of 36% (1.22 g, 2.97 mmol). MP: 163-165° C. (Lit. MP 162.0-162.5° C.); TLC: (AcOEt/cyclohexane 10/90). R_f=0.65; ¹H-NMR (CDCl₃): δ=0.99-1.26 (m, 10H, H(Cy)), 1.60-1.77 (m, 12H, H(Cy)), 3.67 (s, 6H, Me), 6.58 (d, 2H, J=8.2 Hz, H_3' and H_5'), 7.15-7.18 (m, 1H, H(Ar)), 7.18-7.42 (m, 3H, H(Ar)), 7.57 (d, 1H, J=7.4 Hz, H(Ar)) ppm; ¹³C-NMR (CDCl₃): δ=26.5, 27.3, 27.4, 27.6, 29.0, 29.1, 29.8, 30.1, 33.8, 34.0 (C(Cy)), 55.3 (Cb), 103.1 (Ca), 126.2, 128.2, 128.8 (C_3', C_4', C_5'), 130.9, 131.00, 132.4, 135.8 (C₃, C₄, C₅, C₆), 135.8, 136.1, 142.7, 143.1, 157.4 (C_2', C_6') ppm; IR (KBr): υ=3000, 2923, 2851, 1588, 1471, 1442, 1428, 1108 cm^-1.