4-Toluenesulfonyl chloride → 1-(Chloromethyl)-3-nitro-5-(trifluoromethyl)benzene

HRID 2200183ノート

反応式

HRID 2200183 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14]O)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.C1(C)C=CC(S([Cl:32])(=O)=O)=CC=1.CCOC(C)=O>C(Cl)Cl>[Cl:32][CH2:14][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

生成物 1

HCID 684250951-(Chloromethyl)-3-nitro-5-(trifluoromethyl)benzene収率 55%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Dissolve [3-nitro-5-(trifluoromethyl)phenyl]methanol (1.1 g, 5.18 mmol) and triethylamine (1.62 mL) in DCM (20 mL), cool to 0° C., add slowly p-toluenesulfonyl chloride (1.1 g, 6.02 mmol). After the addition, stir the reaction at room temperature for 15 hrs. TLC (EtOAc:PE=1:15) shows the reaction is complete. Concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:15) affords the title compound (655 mg, 55%).

後処理

  1. additionAfter the addition
  2. customthe reaction at room temperature for 15 hrs
  3. concentrationConcentrate under reduced pressure
  4. customto get the crude product
  5. customPurification by chromatography (silica gel, EtOAc:PE=1:15)

出典と根拠

ORDレコード
ord-983bd052bb7842929f7a3543e6f1959e
出典データセット
uspto-grants-2016_06
特許番号
US09359338B2

反応ノート

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