(4-Methoxyphenyl)boronic acid → 7-Hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile

HRID 895232Notes

Reaction equation

HRID 895232 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:13]#[N:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>>[OH:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([C:20]3[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)[CH:3]=[C:4]2[C:13]#[N:14])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 113225983-Bromo-7-hydroxy-1-naphthonitrile

Product 1

HCID 112543667-Hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile

Procedure

The title compound was prepared by. reacting 3-bromo-7-hydroxy-1-naphthonitrile (0.249 g, 1.00 mmol) with 4-methoxyphenylboronic acid (0.21 g, 1.4 mmol) according to Method A to yield 0.19 (69%) of a light yellow solid: mp 226° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.07 (2H, d, J=8.82 Hz), 7.26 (1H, dd, J=2.32 Hz, J=8.90 Hz), 7.37 (1H, d, J=2.27 Hz), 7.80 (2H, d, J=8.80 Hz), 8.02 (1H, d, J=8.96 Hz), 8.37 (1H, d, J=1.85 Hz), 8.44 (1H, d, J=1.43 Hz), 10.48 (1H, bs); MS (ESI) m/z 274 (M−H)−.

Sources & evidence

ORD record
ord-522293073dec49bfbe3471b8060f8372
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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