Cesium carbonate → 1-Bromo-4-chloro-2-(difluoromethoxy)benzene

HRID 2178127Notes

Reaction equation

HRID 2178127 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O.CC(OC)(C)C.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][CH:11]([F:16])[F:15])[CH:4]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 132842722-Bromo-5-chlorophenol

Product 1

HCID 222953811-Bromo-4-chloro-2-(difluoromethoxy)benzeneYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-5-chlorophenol (1 g, 4.8 mmol) in DMF/water (45 mL/5 mL) was added sodium chlorodifluoroacetate (1.95 g, 12.0 mmol) and cesium carbonate (3.14 g, 9.64 mmol), and the reaction mixture was heated to 100° C. for 4 hours. The reaction mixture was cooled and diluted with TBME (20 mL) and water (20 mL). The organic layer was collected, washed with saturated aqueous NaHCO3 solution, brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (1.21 g, 98%), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was collected
  3. washwashed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-745b371fd6164f158f4241b233667c74
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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