(4-Methoxyphenyl)boronic acid → HCID 58978556, compound

HRID 1180334Notes

Reaction equation

HRID 1180334 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 16719446HCID 16719446, compound

Product 1

HCID 58978556HCID 58978556, compound

Procedure

The title compound was prepared by reacting trifluoro-methanesulfonic acid 2-chloro-4-formyl-phenyl ester (5 g, 17.4 mmol) with 4-methoxyphenylboronic acid (3.44 g, 22.6 mmol) according to Method B to yield 3.83 g (89%) of white solid: mp 85-87° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.07 (2H, d, J=8.83 Hz), 7.46 (2H, d, J=8.45 Hz), 7.63 (1H, d, J=7.87 Hz), 7.92 (1H, dd, J=7.87 Hz, J=1.56 Hz), 8.07 (1H, d, J=1.49 Hz); 13C NMR (DMSO-d6): δ 55.14, 113.72, 127.80, 129.72, 130.42, 130.82, 132.15, 132.21, 136.11, 144.90, 159.33, 191.73; IR 1692 cm−1; MS (EI) m/z 246/248 M+.

Sources & evidence

ORD record
ord-c0491445c51c4f8886b344b56debc96f
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

Loading…