Benzo(B)Thiophene → HCID 66608282, compound

HRID 221088Notes

Reaction equation

HRID 221088 reaction equation
CON(C)[C:4](=O)[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[C:12]([F:15])([F:14])[F:13].[CH:18]1[CH:19]=[CH:20][C:21]2[S:26][CH:25]=[CH:24][C:22]=2[CH:23]=1>>[S:26]1[C:25]([CH2:4][C:5]2[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=2[C:12]([F:15])([F:14])[F:13])=[CH:24][C:22]2[CH:23]=[CH:18][CH:19]=[CH:20][C:21]1=2

Participants

3

Reactant 2

HCID 7221Benzo(B)ThiopheneHCID 86028268HCID 86028268, compound

Product 1

HCID 66608282HCID 66608282, compound

Procedure

To a solution of the above N-methoxy-N-methyl-5-bromo-2-iodobenzamide (2.67 g) in N-methyl-2-pyrrolidinone (12 ml) were added copper (I) bromide (124 mg) and methyl fluorosulfonyl(difluoro)acetate (1.34 ml), and the mixture was stirred under heating for 1.5 hours. The reaction mixture was cooled to room temperature, and then, a diluted aqueous ammonia was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-85:15) to give N-methoxy-N-methyl-5-bromo-2-trifluoromethylbenzamide (1.59 g) as colorless oil. APCI-Mass m/Z 312/314 (M+H). (3) The above N-methoxy-N-methyl-5-bromo-2-trifluoromethylbenzamide and thianaphthene were treated in a manner similar to Reference Example 45 to give 1-(Benzo[b]thiophen-2-ylmethyl)-5-bromo-2-trifluoromethylbenzene as a colorless solid. ESI-Mass m/Z 369/371 (M−H).

Sources & evidence

ORD record
ord-63f0974fe94544c38defd339a1c6d0cd
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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