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

HRID 2200183노트

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HRID 2200183 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-983bd052bb7842929f7a3543e6f1959e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359338B2

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