Water → HCID 19622878, compound

HRID 593365Notes

Reaction equation

HRID 593365 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[F:17][CH:18]([F:21])[CH2:19][OH:20].O>CN(C)C=O>[F:17][CH:18]([F:21])[CH2:19][O:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 1361872,2-Difluoroethan-1-ol

Product 1

HCID 19622878HCID 19622878, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave tube a mixture of 1-fluoro-2-nitrobenzene (100 mg, 0.7 mmol), potassium carbonate (193 mg, 1.4 mmol), and 2,2-difluoroethanol in N,N-dimethylformamide (2 ml) was heated in a microwave oven at 120° C. for 20 minutes. For the workup, the reactrion mixture was poured into water (5 ml). The precipitated product was filtered and the aqueous layer was extracted with ether. The combined organic layers were dried and evaporated to yield together with the precipitated material 130 mg (85%) of the 1-(2,2-difluoro-ethoxy)-2-nitro-benzene which was sufficiently pure to be engaged in the next step without further purification; (calculated) C8H7F2NO3 [203.15]; (found) [M+H]+=204.

Workup

  1. filtrationThe precipitated product was filtered
  2. extractionthe aqueous layer was extracted with ether
  3. customThe combined organic layers were dried
  4. customevaporated

Sources & evidence

ORD record
ord-12e15d3483e24038926775fd1c3fe41f
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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