Tert-Butyl hypochlorite → HCID 10713166, compound

HRID 275993Notes

Reaction equation

HRID 275993 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=1[Cl:17].[Cl:18]OC(C)(C)C>ClCCl>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]([Cl:18])[C:5]=1[Cl:17].[Br:1][CH2:2][CH2:3][C:4]1[C:5]([Cl:17])=[CH:6][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([Cl:18])[CH:9]=1

Participants

5

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 10687197HCID 10687197, compound

Product 2

HCID 10713166HCID 10713166, compoundHCID 10736889HCID 10736889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl N-[4-(2-bromoethyl)-3-chlorophenyl]aminoacetate (79 mg) in dichloromethane (2 ml) was added tert-butyl hypochlorite (31 μl) under ice-cooling, and the mixture was stirred for 6 hours at room temperature. The solvent was removed in vacuo, and purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1) gave ethyl N-[4-(2-bromoethyl) -2,3-dichlorophenyl]aminoacetate (31 mg) as a high-polar regioisomer and ethyl N-[4-(2-bromoethyl)-2,5-dichlorophenyl]aminoacetate (34 mg) as a low-polar regioisomer.

Workup

  1. temperaturecooling
  2. customThe solvent was removed in vacuo, and purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-921cf04c27864f6e8da98b66321ccb99
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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