ChemicalBook CAS DataBase List 4-(Bromomethyl)tetrahydropyran

4-(Bromomethyl)tetrahydropyran synthesis

6synthesis methods

Product Name:4-(Bromomethyl)tetrahydropyran
CAS Number:125552-89-8
Molecular formula:C6H11BrO
Molecular Weight:179.05

To a solution of Tetrahydropyran-4-methanol and N-bromobutanimide (NBS) in DCM was added PPh3 at 0°C. The reaction mixture was stirred at room temperature for 1–2h. The resulting mixture was washed with water (20mL) and brine (3×20mL). The organic layer was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in petroleum ether 2–5%) to give 4-(Bromomethyl)tetrahydropyran as a colorless oil.

Tetrahydropyran-4-ylmethyl methanesulfonate

132291-95-3
32 suppliers
$45.00/50mg

125552-89-8
218 suppliers
$11.00/1g

Yield:125552-89-8 81%

Reaction Conditions:

with lithium bromide in water;acetone

Steps:

9 4-(Bromomethyl)oxane
4-(Bromomethyl)oxane (4-Oxanyl)methyl methanesulfonate (12.0 g, 62 mmol) was dissolved in dry acetone (50 mL) and then lithium bromide (32.2 g, 371 mmol) was added. The reaction mixture was refluxed for 6 h under a N₂ atmosphere. The solvent was removed by rotary evaporation. The residue obtained was mixed with water (25 mL) and extracted with dichloromethane (3*25 mL). The combined organic extracts were dried (K₂CO₃), filtered and concentrated by rotary evaporation. The resulting dark brown liquid was distilled (65-70° C., 5 mm) to afford 9.0 g of a colorless liquid (81% yield).

References:

Targacept, Inc. US2004/220214, 2004, A1

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14774-37-9 Synthesis