Carbon tetrabromide → HCID 10498372, compound

HRID 275991Notes

Reaction equation

HRID 275991 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9]O)[CH:5]=[C:4]([Cl:11])[C:3]=1[NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[Br:39][CH2:9][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([Cl:11])[CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10851165ethyl N-[2,6-dichloro-4-(2-hydroxyethyl)phenyl]aminoacetate

Product 1

HCID 10498372HCID 10498372, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl N-[2,6-dichloro-4-(2-hydroxyethyl)phenyl]aminoacetate (650 mg) and triphenylphosphine (700 mg) in dichloromethane (10ml) was added carbon tetrabromide (886 mg) under ice-cooling, and the mixture was stirred for 1 hour. Rough purification of the reaction mixture by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent: hexane/dichloromethane=1/1) gave ethyl N-[4-(2-bromoethyl)-2,6-dichlorophenyl]-aminoacetate (708 mg).

Workup

  1. temperaturecooling
  2. customRough purification of the reaction mixture by flash column chromatography
  3. customon silica gel (eluent: hexane/ethyl acetate=3/1) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent: hexane/dichloromethane=1/1)

Sources & evidence

ORD record
ord-9f5cc3c8029d4fd1be9a9ce905b0c2e5
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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