Ethyl bromoacetate → (2-Bromo-4-trifluoromethyl-phenoxy)-acetic acid ethyl ester

HRID 898584Notes

Reaction equation

HRID 898584 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCN(C(C)C)C(C)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[O:12][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 7748Ethyl bromoacetateHCID 27611682-Bromo-4-(trifluoromethyl)phenol

Product 1

HCID 85969223(2-Bromo-4-trifluoromethyl-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 2.650 g (11.000 mmol) 2-bromo-4-trifluoromethyl-phenol and 1.47 mL 13.20 mmol) ethyl bromo-acetate in 20 mL Hünig base was stirred for 5 h at 120° C. The reaction mixture was diluted with EtOAc and the org. phase was washed with water, saturated aqueous sodium bicarbonate and saturated aqueous NaCl, dried over magnesium sulphate and evaporated down i. vac. Column chromatography (silica gel, gradient dichloromethane/MeOH 100:0→19:1) yielded the product.

Workup

  1. washphase was washed with water, saturated aqueous sodium bicarbonate and saturated aqueous NaCl
  2. dry with materialdried over magnesium sulphate
  3. customevaporated down i
  4. customColumn chromatography (silica gel, gradient dichloromethane/MeOH 100:0→19:1) yielded the product

Sources & evidence

ORD record
ord-b0f172d4b6874120b10e0f4653046180
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

Loading…