Sodium Azide → HCID 117871823, compound

HRID 530583Notes

Reaction equation

HRID 530583 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=2)[OH:14])(=O)=O)=CC=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O>[N:26]([CH2:12][C@@H:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=1)[OH:14])=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 117871296HCID 117871296, compound

Product 1

HCID 117871823HCID 117871823, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

(R)-2-(4-Fluoro-3-(trifluoromethyl)phenyl)-2-hydroxyethyl 4-methylbenzenesulfonate (3.5 g, 9.25 mmol) was dissolved in 20 mL of DMSO. Sodium azide (1.2 g, 18.5 mmol) was added and the mixture was stirred at 80° C. for 3 h. The clear solution was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was dried and concentrated to give (R)-2-azido-1-(4-fluoro-3-trifluoromethylphenyl)-ethanol as a pale brown oil (2.27 g) which was used as is in the next step.

Workup

  1. temperatureThe clear solution was cooled to room temperature
  2. extractionextracted with ethyl acetate and water
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14ce97b3aea2415d8d256b89e77f50d1
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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