Water → HCID 89650216, compound

HRID 2201621Notes

Reaction equation

HRID 2201621 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[CH:4][CH:3]=1.Br[C:11]([F:18])([F:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13].C([O-])([O-])=O.[K+].[K+].O>CC(N(C)C)=O>[F:17][C:11]([F:18])([O:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Br:1])=[CH:3][CH:4]=1)[C:12]([N:14]([CH3:16])[CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27791534-Bromo-3-fluorophenolHCID 13355362HCID 13355362, compound

Product 1

HCID 89650216HCID 89650216, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-5-fluoro-phenol (4.0 g, 20.7 mmol), 2-bromo-2,2-difluoro-N,N-dimethyl-acetamide (4.4 g, 21.6 mmol) and K2CO3 (3.2 g, 23.2 mmol) in 20 mL of DMAC was heated to 100° C. for 120 min. The mixture was then poured on 50 mL of H2O and extracted with TBME (2×50 mL). The combined organic layers were washed with 10% NaOH (50 mL), water and brine and dried over MgSO4. The product (5.7 g, >96% purity by NMR, 17.6 mmol, 85% yield) was obtained as a yellow oil that solidified upon standing.

Workup

  1. extractionextracted with TBME (2×50 mL)
  2. washThe combined organic layers were washed with 10% NaOH (50 mL), water and brine
  3. dry with materialdried over MgSO4
  4. customThe product (5.7 g, >96% purity by NMR, 17.6 mmol, 85% yield) was obtained as a yellow oil

Sources & evidence

ORD record
ord-58ec4d83a4bb461385560e87518e9338
Source dataset
uspto-grants-2016_06
Patent number
US09365495B2

Reaction notes

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