Water → 2-Benzyloxy-4-phenoxy-1-nitrobenzene

HRID 1642623Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[C:19](F)[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:20]=[C:19]([O:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of K2CO3 (0.654 g, 4.74 mmol) in DMF (6 mL) is added 2-benzyloxy-4-fluoro-1-nitrobenzene (0.90 g, 3.64 mmol), followed by phenol (0.343 g, 3.64 mmol). The mixture is stirred at 100° C. for 48 h. The mixture is allowed to cool to ambient temperature, then poured into water and extracted into EtOAc. The organic phase is washed with water (2×), saturated NaCl (1×), and dried over Na2SO4. The solvent is removed under reduced pressure to afford 2-benzyloxy-4-phenoxy-1-nitrobenzene as a pale-yellow solid: mp=96-98° C.; 1H NMR (CDCl3) δ 7.87 (d, J=9.09 Hz, 1H), 7.36-7.23 (m, 7H), 7.20-7.15 (m, 1H), 6.95 (dd, J=8.59, 1.01 Hz, 1H), 6.58 (d, J=2.27 Hz, 1H), 6.46-6.43 (m, 1H), 5.08 (s, 2H).

Workup

temperatureto cool to ambient temperature
extractionextracted into EtOAc
washThe organic phase is washed with water (2×), saturated NaCl (1×)
dry with materialdried over Na2SO4
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-005c6453b6354dfea82cb916a475e7e5
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119666B2

Reaction notes

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