3-Bromo-1-benzothiophene synthesis

6synthesis methods

Product Name:3-Bromo-1-benzothiophene
CAS Number:7342-82-7
Molecular formula:C8H5BrS
Molecular Weight:213.09

95-15-8 Synthesis

95-15-8
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$6.00/5g

7342-82-7
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$5.00/1g

Yield:7342-82-7 100%

Reaction Conditions:

with N-Bromosuccinimide;acetic acid in chloroform at 0 - 20; for 52 h;

Steps:

18.1 Step 1: 3-Bromo-1-benzothiophene
To a solution of benzo[b]thiophene (10 g, 74.5 16 mmol) in chloroform (75 mL) and acetic acid (75 mL), was stepwise added NBS (16.6 g, 93.268 mmol) for 4 hr at 0°C and the mixture allowed to stir at room temperature for 48 hr. The progress of the reaction was monitored by TLC and, after completion of reaction, the reaction mass was diluted with chloroform (200 mL) and the resulting mixture was successively washed with a saturated solution of sodium thiosulfate (200 mL), sodium carbonate (200 mL) and brine (150 mL). The extracted organic layer was then dried over sodium sulfate, filtered and evaporated under reduced pressure. The resulting red liquid was then filtered of a pad of silica gel, eluting with hexane to afford 3-bromo-1-benzothiophene (15.87 g, 74.474 mmol, 100%) as yellow oil. The ‘H NMR and mass was confirmed by reported literature.

References:

CURADEV PHARMA PRIVATE LTD.;BANERJEE, Monali;MIDDYA, Sandip;SHRIVASTAVA, Ritesh;RAINA, Sushil;SURYA, Arjun;YADAV, Dharmendra B.;YADAV, Veejendra K.;KAPOOR, Kamal Kishore;VENKATESAN, Aranapakam;SMITH, Roger A.;THOMPSON, Scott K. WO2014/186035, 2014, A1 Location in patent:Page/Page column 186; 187

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6287-82-7 Synthesis