Sodium Carbonate → 2-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-methyl-naphthalene

HRID 1992965Notes

Reaction equation

HRID 1992965 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[C:3]=1[O:15][CH2:16][O:17][CH3:18].[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:11]([CH3:12])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=3)[C:3]=2[O:15][CH2:16][O:17][CH3:18])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

Product 1

HCID 685374682-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-methyl-naphthaleneYield 98.5%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14) (0.3 g, 0.964 mmol), 4-fluorobenzeneboronic acid (0.27 g, 1.93 mmol), tetrakis(triphenylphosphino)palladium (0) (0.11 g, 0.0964 mmol), 2 M sodium carbonate (5 mL) and ethylene glycol dimethyl ether (5 mL) were added in a sealed tube and reacted as described above to give 0.31 g (96%) of the title compound (203) as a white solid. 1H NMR (400 MHz, d-CDCl3): δ 2.21 (s, 3H), 3.12 (s, 3H), 3.93 (s, 3H), 4.75 (s, 2H), 7.08-7.08 (m, 1H), 7.11-7.17 (m, 3H), 7.30-7.33 (m, 2H), 7.44 (s, 1H), 8.01 (d, J=9.2 Hz, 1H).

Workup

  1. customreacted

Sources & evidence

ORD record
ord-681ab745526647b7bd6128a83b708d8a
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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