Benzo(B)Thiophene → HCID 66608282, compound

HRID 1514554Notes

Reaction equation

HRID 1514554 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-8a89cb07f81c441e9e0dd17d11ca3c68
Source dataset
uspto-grants-2012_07
Patent number
US08222219B2

Reaction notes

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