Carbon tetrabromide → ethyl N-[4-(2-bromoethyl)-2,6-dichlorophenyl]-aminoacetate

HRID 275991ノート

反応式

HRID 275991 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 10498372ethyl N-[4-(2-bromoethyl)-2,6-dichlorophenyl]-aminoacetate収率 89.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9f5cc3c8029d4fd1be9a9ce905b0c2e5
出典データセット
uspto-grants-2002_03
特許番号
US06353025B1

反応ノート

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