Water → 4-Fluoro-2-nitro-1-phenoxybenzene

HRID 16148

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.F[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].O>C1COCC1.C(OCC)(=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Cs2CO3 (12.1 g, 62.9 mmol) was added to a solution of phenol (5.9 g, 62.9 mmol) in 400 mL of THF under N2. After stirring for 15 min. 2,5-difluoronitrobenzene (6.82 mL, 62.9 mmol) in 50 mL of THF was added. The resulting mixture was heated to 40° C. for 25 h. Reaction was followed by HPLC to detect disappearance of 2,5-difluoronitrobenzene. Water and ethyl acetate were added, followed by extraction with ethyl acetate (2×). The combined organic layers were successively washed with saturated aq. sodium bicarbonate (3×), water and brine, dried (Na2SO4) and evaporated. The crude compound was chromatographed on silica to remove excess of phenol. Elution with toluene/ethyl acetate 95:5 gave the title compound (12.6 g, 86%). Data: (m/z)=234 (M+H)+.

Workup

customReaction
extractionfollowed by extraction with ethyl acetate (2×)
washThe combined organic layers were successively washed with saturated aq. sodium bicarbonate (3×), water and brine
dry with materialdried (Na2SO4)
customevaporated
customThe crude compound was chromatographed on silica
customto remove excess of phenol
washElution with toluene/ethyl acetate 95:5

Sources & evidence

ORD record: ord-da4757f359fd416a89ffbefb2b3e25ae
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737136B2

Linked notes

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