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

HRID 399332
Notes
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Reaction equation

HRID 399332 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-9f1f4514115346af92551ecb861db111
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817890

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes