Carbon Dioxide → 2-(Difluoromethoxy)-6-fluorobenzonitrile

HRID 1635688Notes

Reaction equation

HRID 1635688 reaction equation
Cl[CH:2]([F:4])[F:3].[OH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:7]=1[C:8]#[N:9].[OH-].[Na+].C(=O)=O>O.COCCOC>[F:3][CH:2]([F:4])[O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:7]=1[C:8]#[N:9]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 27832162-Fluoro-6-hydroxybenzonitrile

Product 1

HCID 234483612-(Difluoromethoxy)-6-fluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

6.3 g of chlorodifluoromethane were passed into a stirred mixture of 10.0 g of 2-hydroxy-6-fluorobenzonitrile, 50 ml of 1,2-dimethoxyethane and 25 ml of NaOH (33%) at 75° C. (the reflux condenser was cooled with dry ice), and stirring was continued for one hour at 70-75° C. After cooling, the batch was diluted with 300 ml of water and extracted three times using in each case 150 ml of tert-butyl methyl ether. After the solvent had been vaporated, 6.5 9 of the desired product were obtained as an oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times

Sources & evidence

ORD record
ord-544bef124c6e4dc2a36103e2682dc07e
Source dataset
uspto-grants-2003_01
Patent number
US06509501B2

Reaction notes

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