3-Bromo-4-methoxybenzaldehyde → 4-Methoxy-3-(thiophen-2-yl)benzaldehyde

HRID 10653

Reaction equation

HRID 10653 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1B(O)O>>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:13]1[S:12][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 986623-Bromo-4-methoxybenzaldehydeHCID 27339602-Thiopheneboronic acid

Product 1

HCID 219810244-Methoxy-3-(thiophen-2-yl)benzaldehydeYield 96%

Procedure

Ex-41A: 4-Methoxy-3-(thiophen-2-yl)-benzaldehyde was prepared from 3-bromo-4-methoxybenzaldehyde and thiophene-2-boronic acid in a similar manner as described in Ex-3A. Orange oil, 96% yield. 1H-NMR (CDCl3) δ 9.94 (s, 1H), 8.16 (d, J=1.8 Hz, 1H), 7.80 (dd, J=2.4, 8.4 Hz, 1H), 7.57 (dd, J=1.8, 3.6 Hz, 1H), 7.38 (d, J=5.1 Hz, 1H), 7.12 (dd, J=3.6, 5.1 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 4.02 (s, 3H). HRMS m/z: calc. 218.0402, found 218.0406.

Sources & evidence

ORD record
ord-bc3607815f2b4883b3402850fcc9a9b9
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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