Methyl Thioglycolate → Methyl 4,5-dichlorobenzo[b]thiophene-2-carboxylate

HRID 2183656

반응식

HRID 2183656 반응식
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[Cl:7][C:8]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12](F)[C:9]=1[CH:10]=O>CN(C)C=O>[Cl:7][C:8]1[C:9]2[CH:10]=[C:2]([C:1]([O:5][CH3:6])=[O:4])[S:3][C:12]=2[CH:13]=[CH:14][C:15]=1[Cl:16]

참가 물질

4

반응물 2

HCID 16907Methyl ThioglycolateHCID 32600622,3-Dichloro-6-fluorobenzaldehyde

생성물 1

HCID 22474211Methyl 4,5-dichlorobenzo[b]thiophene-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-b6398fb944f24783829a5e112754ac11
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900216B2

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