1,2-Dichloroethane → Ethyl [3,5-bis(trifluoromethyl)phenyl]acetate

HRID 1644777Notes

Reaction equation

HRID 1644777 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:19](O)[CH3:20].C(Cl)CCl>ClCCl>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH2:19][CH3:20])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 702EthanolHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acid

Product 1

HCID 42552891Ethyl [3,5-bis(trifluoromethyl)phenyl]acetateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)phenylacetic acid (24.65 g, 91 mmol) in dichloromethane (150 mL), was added 200 proof ethanol (10.63 mL, 181 mmol), EDC (34.7 g, 181 mmol) and 4-(N,N-dimethylaminopyridine (DMAP, 14.39 g, 118 mmol) at room temperature. The solution was stirred at RT over night, washed with 2 N HCl and saturated aqueous sodium bicarbonate. The organic layer was dried over MgSO4, and the solvent was removed under vacuum to provide 26 g (96%) of the title compound.

Workup

  1. customat room temperature
  2. washwashed with 2 N HCl and saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a69898e972d04838b7d3bc1ea472c263
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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