Dichloromethane → 1-(Benzo[b]thiophen-3-yl)-3-chloropropan-2-one

HRID 1852523Notes

Reaction equation

HRID 1852523 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Al+3].[Cl-].[Cl-].[Cl-].ClC[CH2:16][C:17](Cl)=[O:18].Cl[CH2:21][Cl:22]>>[Cl:22][CH2:21][C:17](=[O:18])[CH2:16][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7221Benzo(B)ThiopheneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 161001791-(Benzo[b]thiophen-3-yl)-3-chloropropan-2-oneYield 85.3%

Procedure

To the solution of benzothiophene (0.05 mol) dissolved in dichloromethane (30 mL), AlCl3 (0.10 mol) is added batch by batch and 3-chloropropionyl chloride (0.055 mol) is added dropwise, while the internal temperature is maintained below 5° C. Following procedures described in General Method One—Method A, 3-chloro-1-(benzothiophen-3- yl)-acetone is obtained as a white solid (9.6 g). The yield is 85.3%. MS(m/z): 225.0 [M+1]+.

Workup

  1. additionis added dropwise, while the internal temperature
  2. temperatureis maintained below 5° C

Sources & evidence

ORD record
ord-c1da22cab2d345e880e6133689856ae5
Source dataset
uspto-grants-2015_02
Patent number
US08962621B2

Reaction notes

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