2-(Benzyloxy) ethanol → Benzene, ((2-bromoethoxy)methyl)-

HRID 1790389Notes

Reaction equation

HRID 1790389 reaction equation
[Br:1]C1C=NNC=1.[H-].[Na+].[CH2:9]([O:16][CH2:17][CH2:18]O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[Br:1][CH2:18][CH2:17][O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 121412-(Benzyloxy) ethanolHCID 163754-BromopyrazoleHCID 24758Sodium hydride

Product 1

HCID 73833Benzene, ((2-bromoethoxy)methyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromopyrazole (2.205 g) was dissolved in tetrahydrofuran (20 ml). Under ice cooling, 60% sodium hydride (625 mg) was added thereto followed by stirring. After 30 min, benzyl 2-bromoethyl ether (3.872 g) obtained from 2-benzyloxyethanol in the same manner as the one of Production Example 1 was added thereto and the resultant mixture was stirred at room temperature overnight. Then the reaction solution was partitioned between ethyl acetate and water and the organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (2.287 g) as a colorless oil (yield: 53%).

Sources & evidence

ORD record
ord-e80df2f9f4ce49b5bd2ee745e5f5299b
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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