3-Fluoro-4-methoxyphenylboronic acid → 8-Chloro-3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile

HRID 1830701Notes

Reaction equation

HRID 1830701 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].[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>>[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:19]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([F:16])[CH:18]=1)=[CH:11]2

Participants

3

Reactant 2

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 114829513-Bromo-8-chloro-7-hydroxy-1-naphthonitrile

Product 1

HCID 114728998-Chloro-3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile

Procedure

The title compound was prepared by reacting 3-bromo-8-chloro-7-hydroxy-1-naphthonitrile (0.20 g, 0.71 mmol) with 3-fluoro-4-methoxyphenylboronic acid (0.17 g, 1.0 mmol) according to Method A to yield 0.14 (60%) of a yellow solid: mp 198–200° C.;1H NMR (DMSO-d6): δ 3.91 (3H, s), 7.27–7.33 (1H, m), 7.45 (1H, d, J=8.93 Hz), 7.71–7.74 (1H, m), 7.85 (1H, dd, J=2.23 Hz, J=13.09 Hz), 8.00 (1H, d, J×9.08 Hz), 8.48 (1H, d, J=1.97 Hz), 8.57 (1H, d, J=1.95 Hz), 11.18 (1H, s); MS (ESI) m/z 326/328 (M−H)−.

Sources & evidence

ORD record
ord-4d5ce44ce9d3485384c525fe75c7ffb7
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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