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

HRID 2200183Notes

Reaction equation

HRID 2200183 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-983bd052bb7842929f7a3543e6f1959e
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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