ChemicalBook CAS DataBase List 6-BROMO-BENZO[B]THIOPHENE

6-BROMO-BENZO[B]THIOPHENE synthesis

15synthesis methods

Product Name:6-BROMO-BENZO[B]THIOPHENE
CAS Number:17347-32-9
Molecular formula:C8H5BrS
Molecular Weight:213.09

Benzo[b]thiophene-3-ol, 6-bromo-2,3-dihydro-

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Yield:17347-32-9 95%

Reaction Conditions:

with boron trifluoride diethyl etherate in acetic acid at 20 - 120; for 0.0833333 h;

Steps:

139.D Example 139; N-[3-(1-Benzo[b]thiophen-6-yl-1-ethyl-propyl)-1H-indol-7-yl]-methanesulfonamide; D. Preparation of: 6-Bromo-benzo[b]thiophene

To a room temperature solution OF 6-BROMO-2, 3-dihydro-benzo [b] thiophen-3-ol (785 mg, 3.39 mmol) in HOAC (7 mL) is added boron trifluoride diethyl etherate (1. 44 G, 10.2 mmol) and the reaction mixture is placed into a 120 C oil bath. After 5 min, the reaction is cooled to room temperature and basified to-pH 11 using 2 M NaOH. The aqueous suspension is extracted with ET2O (2 X 200 mL) and the combined organic layer is dried (MGS04), filtered and concentrated to afford the sub-title compound (689 mg, 95%) as an off-white solid. RF 0. 70 (4: 1 HEX/ETOAC). mp 48-50 C. 'H NMR (300 MHz, CDCl3) 8 7.29 (d, J= 5.4 Hz, 1H), 7.41 (d, J= 5. 4 Hz, 1H), 7.46 (dd, J= = 1. 8,8. 5 Hz, 1H), 7.66 (d, J= 8.5 Hz, 1H), 8.01 (M, 1H).

References:

WO2004/67529,2004,A1 Location in patent:Page 162