3-Bromobenzaldehyde → 3-(2-Thienyl)benzaldehyde

HRID 10655

Reaction equation

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

Participants

Reactant 2

HCID 765833-Bromobenzaldehyde

HCID 27339602-Thiopheneboronic acid

Product 1

HCID 42811003-(2-Thienyl)benzaldehydeYield 93%

Procedure

Ex-42A: 3-(Thiophen-2-yl)-benzaldehyde was prepared from 3-bromobenzaldehyde and thiophene-2-boronic acid in a similar manner as described in Ex-3A. Orange oil, 93% yield. 1H-NMR (CDCl3) δ 10.06 (s, 1H), 8.10 (s, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.78 (d, J=7.2 Hz, 1H), 7.55 (dd, J=7.2, 8.4 Hz, 1H), 7.40 (dd, J=1.5, 3.6 Hz, 1H), 7.34 (dd, J=1.5, 5.3 Hz, 1H), 7.11 (dd, J=3.6, 5.3 Hz, 1H). HRMS m/z: calc. 188.0296. found 188.0293.

Sources & evidence

ORD record: ord-a6f3fe07db1a4753bd3cd731735780b8
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094801B2

Linked notes

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