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

HRID 1992978Notes

Reaction equation

HRID 1992978 reaction equation
Br[C:2]1[C:11]([CH2:12][CH2:13][CH3:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=2)[C:3]=1[O:17][CH2:18][O:19][CH3:20].[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=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:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:11]([CH2:12][CH2:13][CH3:14])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=3)[C:3]=2[O:17][CH2:18][O:19][CH3:20])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 685347832-Bromo-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene

Product 1

HCID 685346522-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-propyl-naphthaleneYield 95.8%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromo-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene (95) (1.26 g, 3.71 mmol), 4-fluorobenzeneboronic acid (1.04 g, 7.43 mmol), tetrakis(triphenylphosphino)palladium (0) (0.43 g, 0.371 mmol), 2 M sodium carbonate (20 mL) and ethylene glycol dimethyl ether (20 mL) were added in a sealed tube and reacted as described above to give 1.26 g (95%) of the title compound (225) as oil. 1H NMR (400 MHz, d-CDCl3): δ 0.80 (t, J=7.3 Hz, 3H), 1.43-1.45 (m, 2H), 2.50 (t, J=7.8 Hz, 2H), 3.11 (s, 3H), 3.93 (s, 3H), 4.73 (s, 2H), 7.10-7.15 (m, 4H), 7.29-7.32 (m, 2H), 7.43 (s, 1H), 8.00 (d, J=8.9 Hz, 1H).

Workup

  1. customreacted

Sources & evidence

ORD record
ord-5bc53fe292274b4286610fb50a63c15c
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…