Bromoacetyl chloride → 5-(Bromoacetyl)-1,3-dihydro-2H-indol-2-one

HRID 620015Notes

Reaction equation

HRID 620015 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][CH2:2][C:3]([C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[NH:6][C:7](=[O:15])[CH2:8]2)=[O:4]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 220993095-(Bromoacetyl)-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromoacetyl chloride (14.17 g) in methylene chloride (30 ml) is added dropwise to a stirred suspension of oxindole (6 g) and AlCl3 (13.31 g) in methylene chloride (200 ml). The reaction mixture is refluxed for 4 hours, cooled to RT, poured with stirring into an ice/water mixture, stirred for 30 minutes, filtered and washed with methylene chloride yielding the desired product as a solid which is recrystallized from isopropanol.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. additionpoured
  3. filtrationfiltered
  4. washwashed with methylene chloride yielding the desired product as a solid which
  5. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-872b31cd40de40e685a749180ebd35b0
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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