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Water → 2-Bromo-2,6-dichloro-6-fluorocyclohexanol

HRID 21828
Notes
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Reaction equation

HRID 21828 reaction equation
B(Br)(Br)[Br:2].[Cl:5][C:6]12O[CH:11]1[CH2:10][CH2:9][C:8]([Cl:14])([F:13])[CH2:7]2.[OH2:15]>ClCCl>[Br:2][C:6]1([Cl:5])[CH2:11][CH2:10][CH2:9][C:8]([Cl:14])([F:13])[CH:7]1[OH:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709682-Bromo-2,6-dichloro-6-fluorocyclohexanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.91 cm3 (2.91 mmol) of BBr3 in molar solution in dichloromethane were introduced at 4° C. under argon atmosphere into 0.98 (5.3 mmol) of epoxide 2e in solution in 6.5 cm3 dichloromethane. The reaction mixture was then allowed to return to room temperature and stirring was continued (1 h 30 min). 5 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): 1.03 g of alcohol 1i were obtained (macrobore GC purity>97%); the yield of product 1i was 73%.

Workup

  1. customto return to room temperature
  2. custom(1 h 30 min)
  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-a254a47f4a7b42b890ab20256a72c77c
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05424460

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes