Water → HCID 89649323, compound

HRID 1467353Notes

Reaction equation

HRID 1467353 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].Br[C:13]([F:20])([F:19])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15].C([O-])([O-])=O.[Na+].[Na+].O>CC(N(C)C)=O>[F:19][C:13]([F:20])([O:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 99375-Fluoro-2-nitrophenolHCID 10340Sodium CarbonateHCID 13355362HCID 13355362, compound

Product 1

HCID 89649323HCID 89649323, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-nitro-5-fluoro-phenol (3.0 g, 19.1 mmol), 2-bromo-2,2-difluoro-N,N-dimethylacetamide (3.9 g, 19.1 mmol) and Na2CO3 (2.1 g, 19.8 mmol) in 30 mL of DMAC was heated to 100° C. overnight. 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) and dried over Na2SO4. The crude product was obtained after evaporation of all volatiles. Purification by chromatography on silica gave the product (1.8 g, 6.4 mmol, 38% yield) 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)
  3. dry with materialdried over Na2SO4
  4. customThe crude product was obtained
  5. customafter evaporation of all volatiles
  6. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-76bdc03a380f403cbef523f907a44d38
Source dataset
uspto-grants-2015_04
Patent number
US09000152B2

Reaction notes

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