1-Chloro-4,5-difluoro-2-nitrobenzene → 1-Chloro-4-fluoro-5-methoxy-2-nitrobenzene

HRID 1831488Notes

Reaction equation

HRID 1831488 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:10]=[C:9](F)[C:8]([F:12])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]>CO>[Cl:4][C:5]1[CH:10]=[C:9]([O:2][CH3:1])[C:8]([F:12])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 101303301-Chloro-4,5-difluoro-2-nitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 220520461-Chloro-4-fluoro-5-methoxy-2-nitrobenzeneYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To sodium methoxide (100 mL of a 0.5 M solution in methanol, 50.1 mmol) cooled to 0° C. was added a solution of 1-chloro-4,5-difluoro-2-nitro-benzene (9.7 g, 50.1 mmol) in methanol (10 mL) dropwise over 15 min. The solution was warmed to room temperature and stirred for 2 h, then poured slowly over ice. The yellow precipitate was collected by filtration and washed with cold water. The crystals were air dried to give 8.2 g (79%) of 1-chloro-4-fluoro-5-methoxy-2-nitro-benzene: Crude 1H NMR (400 MHz, CDCl3): δ 7.85 (d, J=10.5 Hz, 1H), 7.06 (d, J=7.3 Hz, 1H), 3.98 (s, 3H). The crude material was pure enough to carry on to the next step.

Workup

  1. additionpoured slowly over ice
  2. filtrationThe yellow precipitate was collected by filtration
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-4dd41c78ea384e31bf3dfac737e75869
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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