Sodium Hydroxide → 1-Bromo-3-chloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

HRID 21829Notes

Reaction equation

HRID 21829 reaction equation
Cl[C:2]12[O:8][CH:7]1[CH2:6][CH2:5][C:4]([Cl:10])([F:9])[CH2:3]2.[Br:11]C1(Cl)CCCC(Cl)(F)C1O.[OH-].[Na+]>O>[Br:11][C:2]12[O:8][CH:7]1[CH2:6][CH2:5][C:4]([Cl:10])([F:9])[CH2:3]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptaneHCID 189709682-Bromo-2,6-dichloro-6-fluorocyclohexanol

Product 1

HCID 189709431-Bromo-3-chloro-3-fluoro-7-oxabicyclo[4.1.0]heptaneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same procedure was followed as for the production of 2e in Example 17: it was performed with 0.20 g (0.75 mmol) of alcohol 1i, 3 cm3 of water and 0.12 g (3 mmol) of sodium hydroxide. Reaction time: 1 h 15 min; ether extraction (4×7 cm3). After treatment, 0.15 g of epoxide 2g were obtained (macrobore GC purity>97.5%), having a yield of 80%.

Workup

  1. customReaction time
  2. custom1 h 15 min
  3. extractionether extraction (4×7 cm3)

Sources & evidence

ORD record
ord-b199ff4f1c1642b6a42177312296b564
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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