Chloromethyl Methyl Ether → HCID 68536774, compound

HRID 1992947Notes

Reaction equation

HRID 1992947 reaction equation
[Br:1][C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:16].[CH3:17][O:18][CH2:19]Cl.C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:16][CH2:17][O:18][CH3:19]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 68541215HCID 68541215, compound

Product 1

HCID 68536774HCID 68536774, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-3-(trifluoromethyl)-1-naphthalenol (179) (0.23 g, 0.79 mmol) was treated with chloromethyl methyl ether in the presence of diisopropylethylamine in THF to give 0.24 g (91%) of the title compound (180) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.75 (s, 3H), 5.29 (s, 2H), 7.59-7.65 (m, 1H), 7.65-7.71 (m, 1H), 7.91 (d, J=8.1 Hz, 1H), 8.05 (s, 1H), 8.22 (d, J=8.4 Hz, 1H). LCMS (ESI): m/z 335 (M+H)+.

Sources & evidence

ORD record
ord-502e5c8a2150492a880c3372849bfa13
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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