p-Fluoronitrobenzene → 1-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]ethanone

HRID 880350Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([OH:23])[C:10]=1[C:24](=[O:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=2)[C:10]=1[C:24](=[O:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A stirred suspension of 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone (Bulletin of the Chemical Society of Japan (1985), 58(1), 136-41) (5.2 g, 15 mmol), potassium carbonate (3.1 g, 22 mmol) and 1-fluoro-4-nitrobenzene (2.1 g, 15 mmol) in DMF (10 mL) was heated at 110° C. for 2 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and thoroughly washed with brine (4×50 mL). The organic phase was dried over Na2SO4 and then evaporated to dryness. The crude was chromatographed on a small pad of silica gel eluting with hexane/ethyl acetate 5/1, to provide the title compound (5 g, 73% yield).

Workup

washthoroughly washed with brine (4×50 mL)
dry with materialThe organic phase was dried over Na2SO4
customevaporated to dryness
customThe crude was chromatographed on a small pad of silica gel eluting with hexane/ethyl acetate 5/1

Sources & evidence

ORD record: ord-57cf72a171674935abc6e643acba2cd1
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993556B2

Reaction notes

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