1-(2-Amino-5-bromophenyl)ethan-1-one → 1-(2-Amino-5-bromophenyl)-1-(2-furyl)ethanol

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[Li]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:13]1[O:12][CH:16]=[CH:15][CH:14]=1)([OH:11])[CH3:10]

Participants

Reactant 2

HCID 110747461-(2-Amino-5-bromophenyl)ethan-1-one

HCID 178418296HCID 178418296, compound

Product 1

HCID 688651351-(2-Amino-5-bromophenyl)-1-(2-furyl)ethanol

Procedure

Prepared from 1-(2-amino-5-bromo-phenyl)-ethanone and 2-furyl lithium generally according to the procedure described in example 1. 1H-NMR (DMSO-d6) δ 7.6 (m, 1H), 7.08 (dd, J=2.73, 10.91 Hz, 1H), 6.8 (d, J=2.73 Hz, 1H), 6.56 (d, J=8.18 Hz, 1H), 6.45-6.38 (m, 2H), 6.14 (s, 1H), 5.3 (s, 2H), 1.76 (s, 3H); MS (ES) m/z 280/282 ([M−H]−, 30%).

Sources & evidence

ORD record: ord-58dd11db1f5344fc97d935f492230ad7
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323455B2

Reaction notes

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