Chloroacetic Acid → Benzo(B)Thiophene

HRID 128852Notes

Reaction equation

HRID 128852 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.Cl[CH2:11][C:12](O)=O.C(=S)=[S:16]>>[S:16]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:12]=[CH:11]1

Participants

4

Reactant 3

HCID 300Chloroacetic AcidHCID 6348Carbon DisulfideHCID 7416Nitrobenzene

Product 1

HCID 7221Benzo(B)Thiophene

Procedure

In further detail, a compound (XIV) is reacted with a benzoyl chloride in the presence of a Lewis acid (e.g. aluminum chloride or tin tetrachloride) to obtain a compound (XV). Usually, this reaction can be carried out by the use of or without a solvent (e.g. carbon disulfide or nitrobenzene) in a temperature range of room temperature to about 100° C. Then, the compound (XV) is reacted with chloroacetic acid in a temperature range of approximately 80°-130° C. to obtain benzothiophene or a derivative thereof (IIb).

Workup

  1. customUsually, this reaction
  2. customin a temperature range of room temperature to about 100° C

Sources & evidence

ORD record
ord-0598eb82d30840419a233bd41d48e806
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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