Chloromethyl Methyl Ether → 2-Bromo-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene

HRID 1992882Notes

Reaction equation

HRID 1992882 reaction equation
[Br:1][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[OH:17].[CH3:18][O:19][CH2:20]Cl.C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][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]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 68537594HCID 68537594, compound

Product 1

HCID 685347832-Bromo-6-methoxy-1-methoxymethoxy-3-propyl-naphthaleneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-6-(methyloxy)-3-propyl-1-naphthalenol (94) (0.62 g, 2.10 mmol) was treated with chloromethyl methyl ether in the presence of diisopropylethylamine in THF to give 0.66 g (92%) of the title compound (95) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.02 (t, J=7.3 Hz, 3H), 1.65-1.75 (m, 2H), 2.84 (t, J=7.7 Hz, 2H), 3.72 (s, 3H), 3.90 (s, 3H), 5.23 (s, 2H), 7.04 (d, J=2.6 Hz, 1H), 7.12 (dd, J1=9.3 Hz, J2=2.5 Hz, 1H), 7.38 (s, 1H), 8.03 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 361 (M+Na)+, m/z 337 (M−H)−.

Sources & evidence

ORD record
ord-ed1391a7e8024d3faf4d1a4beaca8cef
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…