Water → 2,6-Dichloro-2,6-difluorocyclohexanol

HRID 21827Notes

Reaction equation

HRID 21827 reaction equation
B(Cl)(Cl)[Cl:2].[Cl:5][C:6]1([F:14])[CH2:12][CH2:11][CH:10]2[C:8]([F:13])(O2)[CH2:7]1.[OH2:15]>ClCCl>[Cl:5][C:6]1([F:14])[CH2:12][CH2:11][CH2:10][C:8]([Cl:2])([F:13])[CH:7]1[OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 189709453-Chloro-1,3-difluoro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709542,6-Dichloro-2,6-difluorocyclohexanolYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.36 cm3 (0.55 eq.) of BCl3 in molar solution in dichloromethane were added at 4° C. under argon atmosphere to 0.11 g (0.65 mmol) of epoxide 2f in solution in 3 cm3 of dichloromethane. The reaction mixture was allowed to return to room temperature (1 h), 3 cm3 of distilled water were then added and the mixture was extracted with dichloromethane (4×10 cm3). The extract was dried over MgSO4, filtered and evaporated down. The crude product was purified by flash chromatography on silica (eluent ether/petroleum ether=5/95). 0.08 g of alcohol 1h were obtained having a 60% yield (macrobore GC purity>95%).

Workup

  1. customto return to room temperature
  2. additionwere then added
  3. extractionthe mixture was extracted with dichloromethane (4×10 cm3)
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated down
  7. customThe crude product was purified by flash chromatography on silica (eluent ether/petroleum ether=5/95)

Sources & evidence

ORD record
ord-c96ab045ad4f46e28d2cf88e3e89148f
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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