Potassium Carbonate → 1-Bromo-5-(2,4-difluoro-phenoxy)-2-methyl-3-nitro-benzene

HRID 1818740Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:21][C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[F:13])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

1-Bromo-5-fluoro-2-methyl-3-nitro-benzene (9.40 g, 41.45 mmol) was dissolved in 90 mL dry DMF, and 2,4-difluorophenol (5.93 g, 45.58 mmol) and potassium carbonate (6.70 g, 45.58 mmol) were added. The reaction mixture was placed under nitronge and heated to 120° C. with stirring for 18 hours. The reaction mixture was cooled and concentrated under reduced pressure, and the residue was partitioned between water and EtOAc. The organic phase was separated, washed with 1N aqueous NaOH and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed through silica (0%-6% EtOAc in hexanes) to give 8.484 g of 1-bromo-5-(2,4-difluoro-phenoxy)-2-methyl-3-nitro-benzene.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customthe residue was partitioned between water and EtOAc
customThe organic phase was separated
washwashed with 1N aqueous NaOH and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was chromatographed through silica (0%-6% EtOAc in hexanes)

Sources & evidence

ORD record: ord-25de722ab69c4e259e533aea9d624698
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601726B2

Reaction notes

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