4-Toluenesulfonyl chloride → 1-(3-Nitro-5-(trifluoromethyl)phenyl)ethyl 4-methylbenzenesulfonate

HRID 2200142Notes

Reaction equation

HRID 2200142 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:25]([OH:27])[CH3:26])[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>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:27][CH:25]([C:17]2[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[CH3:26])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 90020647HCID 90020647, compound

Product 1

HCID 900212721-(3-Nitro-5-(trifluoromethyl)phenyl)ethyl 4-methylbenzenesulfonateYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add p-toluenesulfonyl chloride (1.7 g, 8.9 mmol) dropwise at 0° C. to the mixture of 1-(3-nitro-5-(trifluoromethyl)phenyl)ethanol (520 mg, 2.23 mmol) and triethylamine (1.4 g, 13.4 mmol) in dichloromethane (20 mL), stir the resulting mixture for 12 hrs at ambient temperature. Concentrate the mixture under reduced pressure to get a residue, purify the residue by chromatography (silica gel, EtOAc:PE=1:10) to afford the title compound (700 mg, 80.6%).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. customto get a residue
  3. custompurify the residue by chromatography (silica gel, EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-5b1a1e6a98ea45049fbf43d95f007627
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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