3-Bromophenetole → Methanol

HRID 1392991Notes

Reaction equation

HRID 1392991 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:11][C:12]1[CH:23]=[CH:22][C:15]([C:16](N(OC)C)=[O:17])=[CH:14][CH:13]=1>>[CH3:4][OH:8].[Br:11][C:12]1[CH:23]=[CH:22][C:15]([C:16]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH3:10])[CH:3]=2)=[O:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 758673-BromophenetoleHCID 109992524-Bromo-N-methoxy-N-methylbenzamide

Product 2

HCID 887MethanolYield 47%HCID 69198022HCID 69198022, compound

Procedure

The title compound was prepared from 3-bromophenetole and 4-bromo-N-methoxy-N-methylbenzamide following the general method of Method 1. The crude product was re-crystallized from methanol affording 0.37 g (47% yield) of the title compound as colorless crystals: mp 68.5-70.1° C.; 1H NMR (400 MHz, CDCl3) δ 7.70-7.60 (m, 4 H), 7.38 (broad t, J=7.6 Hz, 1 H), 7.31-7.27 (m, 2 H), 7.13 (ddd, J=8.2, J=2.3, J=1.2 Hz, 1 H), 4.08 (q, J=7.0 Hz, 2 H), 1.43 (t, J=7.0 Hz, 3 H); 13C NMR (400 MHz, CDCl3) δ 195.5, 159.0, 138.4, 136.4, 131.6, 131.5, 129.3, 127.5, 122.5, 119.5, 114.9, 63.7, 14.7; MS (TSP) m/z 305 (M+1).

Sources & evidence

ORD record
ord-6cd0d8900e9f435893c885b7d7c30d81
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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