Water → HCID 67170971, compound

HRID 1918356Notes

Reaction equation

HRID 1918356 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[F:15][C:16]1([F:21])[CH2:19][CH:18]([OH:20])[CH2:17]1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([O:20][CH:18]2[CH2:19][C:16]([F:21])([F:15])[CH2:17]2)=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 225009543,3-Difluorocyclobutanol

Product 1

HCID 67170971HCID 67170971, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of Methyl 4-fluoro-3-nitrobenzoate, 1.6 g of 3,3-Difluoro-cyclobutanol, and 3.3 g of Cs2CO3 were stirred in 10 ml of anhydrous DMF for 7 h at 60° C. The reaction mixture was then poured into 100 ml of water and extracted three times using 30 ml of EA each. The organic layer was dried using MgSO4 and volatiles were evaporated to yield 1.4 g of the title compound that was used without further purification.

Workup

  1. extractionextracted three times
  2. customThe organic layer was dried
  3. customwere evaporated

Sources & evidence

ORD record
ord-03bf152b20e74a9aa1f2e8b7b7911dd1
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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