Water → 4-(Bromomethyl)-1,1-difluorocyclohexane

HRID 1443603Notes

Reaction equation

HRID 1443603 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]2[CH2:17][CH2:16][C:15]([F:19])([F:18])[CH2:14][CH2:13]2)(=O)=O)=CC=1.O.[Br-:22].[Li+].O>CC(C)=O>[Br:22][CH2:11][CH:12]1[CH2:17][CH2:16][C:15]([F:19])([F:18])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 23224632(4,4-Difluorocyclohexyl)methyl 4-methylbenzenesulfonateHCID 23702478Lithium bromide hydrate

Product 1

HCID 533503614-(Bromomethyl)-1,1-difluorocyclohexaneYield 72.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 15 ml of acetone, 1.5 g of 4,4-difluorocyclohexylmethyl p-toluenesulfonate was dissolved. Thereto 1.6 g of lithium bromide monohydrate was added and the mixture was heated under reflux for 8 hours. After the reaction mixture was cooled to room temperature, water was added and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.76 g of 4-bromomethyl-1,1-difluorocyclohexane.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. extractionthe mixture was extracted with t-butyl methyl ether
  4. washThe organic layer was washed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2976c8297e0242aba5c661d1567f0e3a
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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