Chloromethyl Methyl Ether → 2-Bromo-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-3-(3,3,3-trifluoropropyl)naphthalene

HRID 1992904Notes

Reaction equation

HRID 1992904 reaction equation
[Br:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][CH3:19])[CH:8]=2)[C:3]=1[OH:20].[CH3:21][O:22][CH2:23]Cl.C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][CH3:19])[CH:8]=2)[C:3]=1[O:20][CH2:21][O:22][CH3:23]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 685362622-Bromo-6-(methyloxy)-3-(3,3,3-trifluoropropyl)-1-naphthalenol

Product 1

HCID 685376072-Bromo-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-3-(3,3,3-trifluoropropyl)naphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-6-(methyloxy)-3-(3,3,3-trifluoropropyl)-1-naphthalenol (122) (0.47 g, 1.35 mmol) was treated with chloromethyl methyl ether in the presence of diisopropylethylamine in THF to give 0.42 g (80%) of the title compound (123) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 2.40-2.55 (m, 2H), 3.10-3.20 (m, 2H), 3.72 (s, 3H), 3.91 (s, 3H), 5.23 (s, 2H), 7.04 (d, J=2.6 Hz, 1H), 7.16 (dd, J1=9.3 Hz, J2=2.5 Hz, 1H), 7.43 (s, 1H), 8.03 (d, J=9.3 Hz, 1H).

Sources & evidence

ORD record
ord-3c9b3f0c2e694498a054d9f446285003
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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