Chloromethyl Methyl Ether → HCID 68537292, compound

HRID 1992911Notes

Reaction equation

HRID 1992911 reaction equation
[Br:1][C:2]1[C:11]([CH2:12][CH2:13][CH3:14])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:17])=[C:7]([O:15][CH3:16])[CH:8]=2)[C:3]=1[OH:18].[CH3:19][O:20][CH2:21]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][C:6]([F:17])=[C:7]([O:15][CH3:16])[CH:8]=2)[C:3]=1[O:18][CH2:19][O:20][CH3:21]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 68537263HCID 68537263, compound

Product 1

HCID 68537292HCID 68537292, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-7-fluoro-6-(methyloxy)-3-propyl-1-naphthalenol (134) (0.52 g, 1.66 mmol) was treated with chloromethyl methyl ether in the presence of diisopropylethylamine in THF to give 0.49 g (83%) of the title compound (135) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.01 (t, J=7.3 Hz, 3H), 1.65-1.75 (m, 2H), 2.83 (t, J=7.8 Hz, 2H), 3.72 (s, 3H), 3.98 (s, 3H), 5.21 (s, 2H), 7.10 (d, J=8.3 Hz, 1H), 7.37 (s, 1H), 7.76 (d, J=12.4 Hz, 1H). LCMS (ESI): m/z 379 (M+Na)+.

Sources & evidence

ORD record
ord-1ae416b9f4a54f7ca07f7043447d0e72
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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