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

HRID 2200146Notes

Reaction equation

HRID 2200146 reaction equation
S([Cl:11])(C1C=CC(C)=CC=1)(=O)=O.[N+:12]([C:15]1[CH:16]=[C:17]([CH2:25]O)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)([O-:14])=[O:13].C(N(CC)CC)C>ClCCl>[Cl:11][CH2:25][C:17]1[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add slowly tosyl chloride (1.1 g, 6.02 mmol) to the mixture of (3-nitro-5-(trifluoromethyl)phenyl)methanol (1.1 g, 5.18 mmol) and triethylamine (1.62 mL) in dichloromethane (20 mL) at 0° C., stir the resulting mixture for 15 hrs at room temperature. Concentrate the mixture to obtain the crude product, purify by flash chromatography (silica gel, EtOAc:PE=1:15) to afford the title compound (655 mg, 55%).

Workup

  1. concentrationConcentrate the mixture
  2. customto obtain the crude product
  3. custompurify by flash chromatography (silica gel, EtOAc:PE=1:15)

Sources & evidence

ORD record
ord-9a6cf053fe5d473cbd6b29bb9d7a873d
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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