Water → 2-Difluoromethoxy-6-propylsulfanylbenzonitrile

HRID 229931Notes

Reaction equation

HRID 229931 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH2:11][CH2:12][CH3:13])[C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH:21]([F:23])[F:22].O>CN(C)C=O>[F:22][CH:21]([F:23])[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH2:11][CH2:12][CH3:13])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 62407Bromodifluoromethane2×HCID 685669922-Hydroxy-6-propylsulfanylbenzonitrile

Product 1

HCID 685651162-Difluoromethoxy-6-propylsulfanylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.8 g (56 mmol) of 2-hydroxy-6-propylsulfanylbenzonitrile were dissolved in 120 ml of dimethylformamide, and 15.5 g (0.11 mol) of anhydrous potassium carbonate were added. Then, at room temperature, 8.2 g of bromodifluoromethane were passed in, and the mixture was stirred at room temperature for 5 hours. Then 15.5 g (0.11 mol) of anhydrous potassium carbonate and 7.2 g of bromodifluoromethane were added, and the mixture was stirred at room temperature overnight. The reaction mixture was worked up by pouring into water and extracting twice with methyl tert.-butyl ether. The organic phase was separated, washed several times with water and concentrated. The solid has been dried in vacuo at 50° C. Yield: 12.3 g of an oily residue.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracting twice with methyl tert.-butyl ether
  4. customThe organic phase was separated
  5. washwashed several times with water
  6. concentrationconcentrated
  7. customThe solid has been dried in vacuo at 50° C

Sources & evidence

ORD record
ord-8e25aa662d4b4dae9d49c8245bd9d31e
Source dataset
uspto-grants-2009_07
Patent number
US07563921B2

Reaction notes

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