Sodium Carbonate → 6-Methoxy-1-methoxymethoxy-3-methyl-2-(3-trifluoromethyl-phenyl)-naphthalene

HRID 1992967Notes

Reaction equation

HRID 1992967 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]([F:31])([F:30])[C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=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>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]([O:15][CH2:16][O:17][CH3:18])=[C:2]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([C:20]([F:31])([F:30])[F:19])[CH:26]=1)[C:11]([CH3:12])=[CH:10]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

Product 1

HCID 685374636-Methoxy-1-methoxymethoxy-3-methyl-2-(3-trifluoromethyl-phenyl)-naphthaleneYield 99%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14) (0.5 g, 1.61 mmol), 3-trifluoromethylbenzeneboronic acid (0.61 g, 3.21 mmol), tetrakis(triphenylphosphino)palladium (0) (0.186 g, 0.161 mmol), 2 M sodium carbonate (15 mL) and ethylene glycol dimethyl ether (15 mL) were added in a sealed tube and reacted as described above to give 0.60 g (99%) of the title compound (208) as a white solid. 1H NMR (400 MHz, d-CDCl3): δ 2.21 (s, 3H), 3.01 (s, 3H), 3.93 (s, 3H), 4.76 (s, 2H), 7.09 (m, 1H), 7.12-7.15 (dd, J1=2.5 Hz, J2=9.1 Hz, 1H), 7.45 (s, 1H), 7.55-7.65 (m, 4H), 7.98 (d, J=9.2 Hz, 1H).

Workup

  1. customreacted

Sources & evidence

ORD record
ord-11cb924544ed4949ac53ad3e61693d53
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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