Phenyltrimethylammonium bromide dibromide → HCID 22473722, compound
Reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11](=[O:14])[CH2:12][CH3:13])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br-:15].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>>[Br:15][CH:12]([CH3:13])[C:11]([C:9]1[S:8][C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=2[CH:10]=1)=[O:14]Participants
3
Procedure
In a similar manner to Example 18, methylthioglycolate (13 g) was reacted with 3-chloro-2-fluorobenzaldehyde (19.57 g) in dimethylformamide to give methyl 7-chlorobenzo[b]thiophene-2-carboxylate, which was hydrolysed, chlorinated and reacted with N,O-dimethylhydroxylamine hydrochloride to give 7-chloro-N-methoxy-N-methylbenzo[b]thiophene-2-carboxamide, which was reacted with ethylmagnesium bromide to give 1-(7-chlorobenzo[b]thiophen-2-yl)propan-1-one. This ketone (1.17 g) was reacted with phenyltrimethylammonium tribromide (2.15 g) to give 2-bromo-1-(7-chlorobenzo[b]thiophen-2-yl)propan-1-one (2.32 g) which was used without further purification.
Sources & evidence
- ORD record
- ord-dce7380ed39c4a349b587914d2adadf4
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900216B2
Reaction notes
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