Cesium carbonate → HCID 79018268, compound

HRID 1747507Notes

Reaction equation

HRID 1747507 reaction equation
Cl[C:2]([F:7])([F:6])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:15][C:16]1[CH:17]=[CH:18][C:19]([OH:24])=[C:20]([CH:23]=1)[C:21]#[N:22]>CN(C=O)C.O>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:24][CH:2]([F:6])[F:7])=[C:20]([CH:23]=1)[C:21]#[N:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 27570145-Bromo-2-hydroxybenzonitrile

Product 1

HCID 79018268HCID 79018268, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium chloro(difluoro)acetate (9.62 g, 63.1 mmol) and cesium carbonate (12.3 g, 37.9 mmol) were added to a mixed solution of 5-bromo-2-hydroxybenzonitrile (5.00 g, 25.2 mmol) in DMF (50 mL) and water (5 mL), and the mixture was stirred at 100° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2] to obtain the title compound (3.83 g, yield: 61%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2]

Sources & evidence

ORD record
ord-5bf2bfb8721344f8aa8ca2ac7ca4c0df
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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