Chlorodifluoromethane → Methyl 4-(difluoromethoxy)-3-fluorobenzoate

HRID 1386944Notes

Reaction equation

HRID 1386944 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.Cl[CH:14]([F:16])[F:15].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:14]([F:16])[F:15])=[C:6]([F:11])[CH:5]=1

Participants

5

Reactant 4

HCID 6372ChlorodifluoromethaneHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 69829897Methyl 4-(difluoromethoxy)-3-fluorobenzoateYield 83%

Procedure

A solution of 3-fluoro-4-hydroxy-benzoic acid methyl ester (2 g, 11.75 mmol), chlorodifluoromethane (10.6 g, 122.6 mmol, 10.4 eq.) and K2CO3 (1.94 g, 14.1 mmol) was heated in an autoclave for 6 hrs. at 160° C. After cooling the mixture was treated with excess Na2CO3 and extracted with EtOAc. The organic phase was washed twice with satd. NaCl then dried and evaporated to afford the title compound (2.14 g, 83% yield) as an orange oil. MS: m/e=220 (M+).

Workup

  1. customat 160° C
  2. temperatureAfter cooling the mixture
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed twice with satd
  5. dry with materialNaCl then dried
  6. customevaporated

Sources & evidence

ORD record
ord-74e308c2224049e69aace3313f98fc2c
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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