Methyl iodide → Methyl 4,4'-difluorobenzilate

HRID 2099341Notes

Reaction equation

HRID 2099341 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[O-][CH2:21]C.[Na+].[Na].CI>C(O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)([OH:10])[C:7]([O:9][CH3:21])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 12068839Bis(4-fluorophenyl)(hydroxy)acetic acid

Product 1

HCID 12068840Methyl 4,4'-difluorobenzilate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.0 g (0.095 mol) of 4,4′-difluorobenzilic acid are added to freshly prepared sodium ethoxide solution containing 2.17 g (0.095 mol) of sodium and 200 mL of ethanol at 20° C. and stirred for 3 h. The solution is evaporated to dryness, the residue is dissolved in DMF, 22.57 g (0.16 mol) of methyl iodide are added dropwise at 20° C. and the mixture is stirred for 24 h. It is worked up and purified analogously to compound 3b. Yield: 21.06 g of 11 (80% of theory).

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in DMF
  3. stirringthe mixture is stirred for 24 h
  4. custompurified analogously to compound 3b

Sources & evidence

ORD record
ord-3503d900892f41eba752f339466c8174
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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