Trichloroethanol → HCID 19601380, compound

HRID 610447Notes

Reaction equation

HRID 610447 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:26][C:27]([Cl:31])([Cl:30])[CH2:28]O>ClCCl>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:28][C:27]([Cl:31])([Cl:30])[Cl:26])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8259TrichloroethanolHCID 9845Trifluoroacetic anhydrideHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 19601380HCID 19601380, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromomethylphenylacetic acid (12) (10.3 g, 44.8 mmol) was suspended in dichloromethane (30 ml). Trifluoroacetic anhydride (9.28 ml, 67.2 mmol) was added at 0° C., and the resulting mixture was stirred for 30 min. Then, 2,2,2-trichloroethanol (6.47 ml, 67.2 mmol) was added dropwise, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a colorless oil. The oil was left standing overnight to give 2,2,2-trichloroethyl 4-bromomethylphenylacetate (13) as white crystals (15.9 g, yield 98%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washThe reaction mixture was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a colorless oil
  6. waitThe oil was left
  7. waitstanding overnight

Sources & evidence

ORD record
ord-f3f73bfa087d456e80ef46a2bda09f8f
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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