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ChemicalBook CAS DataBase List 7-BROMOMETHYL-BENZO[B]THIOPHENE

7-BROMOMETHYL-BENZO[B]THIOPHENE synthesis

2synthesis methods
-

Yield: 61%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 110; for 1 h;Irradiation;

Steps:

8
A stirred, heated (110°C) solution of 7-methyl-benzo [b] thiopl1ene (4.98g, 33. 6mmol), N-bromosuccinimide (4.97g, 30. 3mmol), and 2,2'-azobisisobutyronitrile (0. 500 g, 2. 81mmol) in carbon tetrachloride (150ml) is irradiated with a sun lamp for 1 hour. The reaction is cooled to ambient temperature and methanol added until the solution is homogeneous. The solution is concentrated onto silica gel and purified via flash chromatography eluting with 100% hexanes to afford a solid (5.07g) which is further purified by recrystallization from hexanes with cooling in the freezer to afford 7- bromomethyl-benzo [b] thiophene as a colourless solid (4. 21 g, 61 %). 1H NMR (CDC13) : 8 = 7.81 (1H, dd), 7.50 (1H, d), 7.41-7. 34 (3H, m), 4.79 (2H, s).

References:

ELI LILLY AND COMPANY WO2005/92885, 2005, A1 Location in patent:Page/Page column 51