Phenol → 4-Bromo-2-phenoxybenzaldehyde

HRID 51588

Reaction equation

HRID 51588 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:18]C1C=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:18][C:3]1[CH:2]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 5770ReserpineHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 286023532-(3-Bromophenoxy)benzonitrile

Product 1

HCID 164134294-Bromo-2-phenoxybenzaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared in a 46% yield from 5-bromo-2-fluoro-benzaldehyde and phenol in a manner similar to that described for the preparation of 5-bromo-phenoxybenzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 10.32(s, 1H), 7.92(s, 1H), 7.81(d, 1H), 7.46(t, 2H), 7.27(t, 1H), 7.18(d, 2H), 6.90(d, 1H) 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 13.08 min.

Workup

  1. customtr 13.08 min.

Sources & evidence

ORD record
ord-34160c193bba4f8993363aa30d6abc90
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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