Toluene → (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

HRID 1489912Notes

Reaction equation

HRID 1489912 reaction equation
CS(O)(=O)=O.C1(C)C=CC=CC=1.[F:13][CH:14](F)[C:15](C(OC(C)(C)C)=O)([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:16](OCC)=[O:17]>O>[F:13]/[CH:14]=[C:15](\[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)/[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 6395Methanesulfonic AcidHCID 15342051Ethyl 2-(difluoromethyl)-2-(t-butoxycarbonyl)-4-(p-fluorophenyl)butyrate

Product 1

HCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add methanesulfonic acid (47.7 kg, 496 mol) to a toluene solution of ethyl 2-(difluoromethyl)-2-(t-butoxycarbonyl)-4-(p-fluorophenyl)butyrate as prepared in Example 3.1 at a temperature of 40° C.-50° C. After 3 to 6 hours, cool the reaction to ambient temperature. Add toluene (91 kg) and water (421 kg) and stir for 30 minutes. Separate the aqueous layer. Add to the organic layer a 20% by weight solution of sodium chloride in water (420 kg) and stir for 30 minutes. Separate the layers to give the title compound as a solution in toluene.

Workup

  1. customas prepared in Example 3.1 at a temperature of 40° C.-50° C
  2. temperaturecool
  3. customthe reaction to ambient temperature
  4. customSeparate the aqueous layer
  5. additionAdd to the organic layer a 20% by weight solution of sodium chloride in water (420 kg)
  6. customSeparate the layers

Sources & evidence

ORD record
ord-e2700ddf1f5b487f83cc8bba401518fe
Source dataset
uspto-grants-1997_10
Patent number
US05679854

Reaction notes

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