Diethyl Ether → 4-(2',6'-Dimethoxyphenyl)-2-nitrobenzyl bromide

HRID 2185947

反応式

HRID 2185947 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:48])C(=O)C1.CCOCC>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][Br:48])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 700560064-(2',6'-Dimethoxyphenyl)-2-nitrobenzyl alcohol

生成物 1

HCID 224521184-(2',6'-Dimethoxyphenyl)-2-nitrobenzyl bromide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1.8 g (6.23 mmol) of 4-(2′,6′-dimethoxyphenyl)-2-nitrobenzyl alcohol and 2.3 g (8.72 mmol) of Ph3P in CH2Cl2 (20 mL) at 0° C. was added 1.32 g (7.5 mmol) of NBS. The reaction mixture was stirred at 0° C. for 30 min at which time TLC analysis (eluted with 25% Et2O in hexanes) indicated that the starting material had been consumed. The reaction mixture was concentrated and the crude residue was purified by flash column chromatography on silica gel eluted with 50% Et2O in hexanes to give 4-(2′,6′-dimethoxyphenyl)-2-nitrobenzyl bromide as a pale yellow solid. Trituration with hexanes gave the product as a white solid.

後処理

  1. customhad been consumed
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude residue was purified by flash column chromatography on silica gel
  4. washeluted with 50% Et2O in hexanes

出典と根拠

ORDレコード
ord-ce7d3c1d5e7e469d8f1217d26e5b77e2
出典データセット
uspto-grants-2002_06
特許番号
US06403584B1

関連ノート

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