Water → 3,3-Difluoro-3-methoxy-2-trifluoromethylpropene

HRID 492275Notes

Reaction equation

HRID 492275 reaction equation
[CH2:1](N(CC)CC)C.[CH2:8]=[C:9]([C:14]([O:17]S(F)(=O)=O)([F:16])[F:15])[C:10]([F:13])([F:12])[F:11].O>CO>[F:15][C:14]([F:16])([O:17][CH3:1])[C:9]([C:10]([F:13])([F:12])[F:11])=[CH2:8]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 87741755CH2=C(CF3)CF2Oso2F

Product 1

HCID 865909533,3-Difluoro-3-methoxy-2-trifluoromethylpropeneYield 51.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (2.5 g, 0.02 mole) is added gradually to CH2═C(CF3)CF2OSO2F (5 g, 0.02 mole) in dry methanol (10 ml) at 10° C. After 20 minutes the reaction mixture is poured into water. The organic layer is separated, washed in turn in dilute aqueous HCl, water, sodium bicarbonate solution, and water, and then dried over MgSO4. Distillation of the dried mixture gives 3,3-difluoro-3-methoxy-2-trifluoromethylpropene (1.8 g, 50% yield). The isomer 1,1-difluoro-2-trifluoromethyl-3-methoxypropene (about 1%) and CH2═C(CF3)COOCH3 (about 3%) are also detected by gas chromatography-mass spectrometry (GC-MS).

Workup

  1. customThe organic layer is separated
  2. washwashed in turn in dilute aqueous HCl
  3. dry with materialwater, sodium bicarbonate solution, and water, and then dried over MgSO4
  4. distillationDistillation of the dried mixture

Sources & evidence

ORD record
ord-512dccee168a482bac759cd65077d648
Source dataset
uspto-grants-2009_05
Patent number
US07531689B2

Reaction notes

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