HCID 22474185, compound → HCID 22473850, compound
Reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](N(OC)C)=[O:12])[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:17].[CH2:18]([Mg]Br)[CH3:19]>>[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](=[O:12])[CH2:18][CH3:19])[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:17]Participants
3
Procedure
In a similar manner to Example 18, methyl thioglycolate (9.3 ml) was reacted with 2,3-dichloro-6-fluorobenzaldehyde (15.46 g) in dimethylformamide to give methyl 4,5-dichlorobenzo[b]thiophene-2-carboxylate (7.28 g) as an off-white solid which was hydrolysed, chlorinated and reacted with N,O-dimethylhydroxylamine hydrochloride to give 4,5-dichloro-N-methoxy-N-methylbenzo[b]thiophene-2-carboxamide (1.96 g) as a colourless solid. Reaction of this amide with ethylmagnesium bromide gave 1-(4,5-dichlorobenzo[b]thiophen-2-yl)propan-1-one (1.09 g) as an oil which was used without further purification.
Sources & evidence
- ORD record
- ord-7790b91c8a6447d7928a08874f1bf1a0
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900216B2
Reaction notes
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