4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride) → 8-Chloro-7-hydroxy-3-(4-hydroxy-phenyl)-naphthalene-1-carbonitrile

HRID 895258Notes

Reaction equation

HRID 895258 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]#[N:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[C:6]=2[Cl:13].[Si]([O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(C(C)(C)C)(C)C>>[Cl:13][C:6]1[C:7]([OH:12])=[CH:8][CH:9]=[C:10]2[C:5]=1[C:4]([C:14]#[N:15])=[CH:3][C:2]([C:27]1[CH:28]=[CH:29][C:24]([OH:23])=[CH:25][CH:26]=1)=[CH:11]2

Participants

3

Reactant 2

HCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 114829513-Bromo-8-chloro-7-hydroxy-1-naphthonitrile

Product 1

HCID 102364508-Chloro-7-hydroxy-3-(4-hydroxy-phenyl)-naphthalene-1-carbonitrile

Procedure

The title compound was prepared by reacting 3-bromo-8-chloro-7-hydroxy-1-naphthonitrile (0.10 g, 0.37 mmol) with 4-tert-butyldimethylsilyloxyphenylboronic acid (0.13 g, 0.52 mmol) according to Method A to yield 0.036 g (33%) of a white solid: mp 254-256° C.; 1H NMR (DMSO-d6): δ 6.90 (2H, d, J=8.64 Hz), 7.43 (1H, d, J=8.95 Hz), 7.72 (2H, d, J=8.64 Hz), 7.99 (1H, d, J=8.97 Hz), 8.38 (1H, d, J=1.95 Hz), 8.47 (1H, d, J=1.92 Hz), 9.73 (1H, s), 11.08 (1H, s); MS (ESI) m/z 294/296 (M−H)−.

Sources & evidence

ORD record
ord-74a98ef7b564454b9cc1f98f282ddb10
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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