Sodium Azide → 4-Azidomethyl-1,1-difluorocyclohexane

HRID 639497Notes

Reaction equation

HRID 639497 reaction equation
[F:1][C:2]1([F:20])[CH2:7][CH2:6][CH:5]([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][CH2:3]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.ClCCl>[N:21]([CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([F:20])([F:1])[CH2:3][CH2:4]1)=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 23224632(4,4-Difluorocyclohexyl)methyl 4-methylbenzenesulfonate

Product 1

HCID 866284444-Azidomethyl-1,1-difluorocyclohexane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of toluene-4-sulfonic acid 4,4-difluorocyclohexylmethyl ester (100 mg, 0.33 mmol)) in N,N-Dimethylformamide (0.5 mL) was added sodium azide (32 mg, 0.49 mmol). The reaction mixture was stirred at 90° C. for 90 min, cooled to room temperature and diluted with dichloromethane (5 mL). The organic layer was washed with water (2×5 mL), collected, dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water (2×5 mL)
  3. customcollected
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03277e1e80034c9ca1e7975d47e3356a
Source dataset
uspto-grants-2010_04
Patent number
US07691878B2

Reaction notes

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