Water → HCID 67170971, compound

HRID 1475767Notes

Reaction equation

HRID 1475767 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-667114387d084bd3af60c836a1fceff1
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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