Toluene → 1-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

HRID 1099053Notes

Reaction equation

HRID 1099053 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([OH:11])[OH:10])=[CH:4][C:3]=1[F:13].C([O-])([O-])O[CH2:16][CH3:17].[C:20]1(C)C=CC=C[CH:21]=1>C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([O:10][CH2:16][CH3:17])[O:11][CH2:20][CH3:21])=[CH:4][C:3]=1[F:13]

Participants

6

Reactant 3

HCID 1140TolueneHCID 53630039EthylorthoformateHCID 575165211-(4-Bromo-3-fluorophenyl)-2,2-dihydroxyethanone

Product 1

HCID 575165221-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanoneYield 93%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromo-3-fluorophenyl)-2,2-dihydroxyethanone (3.5 g, 0.014 mol) in toluene (30 mL) was added ethyl orthoformate (5.8 mL, 0.035 mol) and p-toluenesulfonic acid (100 mg). The reaction was refluxed for 4 h. After cooled to RT, the mixture was diluted with ethyl acetate, washed with saturated NaHCO3 solution, water, and brine, dried over MgSO4, filtered and concentrated to give the product (4.0 g, 93%) which was used in the next step without further purification.

Workup

  1. temperatureThe reaction was refluxed for 4 h
  2. washwashed with saturated NaHCO3 solution, water, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db7de1d8826a4f0bb737fc336ebbfbc8
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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