Phenol → 4-Bromo-2-nitro-1-phenoxybenzene

HRID 51585Notes

Reaction equation

HRID 51585 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.BrC1C=CC=C(C=1)OC1C=CC=CC=1C#N.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 5770ReserpineHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 286023532-(3-Bromophenoxy)benzonitrile

Product 1

HCID 161094494-Bromo-2-nitro-1-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared in a quantitative yield from 5-bromo-2-fluoro-nitrobenzene and phenol in a manner similar to that described for the preparation of 5-bromo-phenoxybenzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 8.31 9d, 1H), 7.86(dd, 1H), 7.45(t, 2H), 7.25(t, 1H), 7.13(d, 1H), 7.08(d, 2H); RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 12.70 min.

Workup

  1. customtr 12.70 min.

Sources & evidence

ORD record
ord-a850122be84941f2be7e2f07be81dafe
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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