Water → 2-(1-Methylcyclohexyl)-4-bromoanisole

HRID 1651320Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:3]=1.[H-].[Na+].[CH3:18]I.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:18])=[C:4]([C:9]2([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The 4-bromo-2-(1-methylcyclohexyl) phenol (9.26 g, 34.4 mmoles) is dissolved in 50 ml of THF. The solution is cooled to 0° C. and there is added in small fractions sodium hydride (80% in oil, 1.14 g, 37.8 mmoles). The reaction mixture is stirred for 30 minutes at ambient temperature and 5.37 g (37.8 mmoles) of methyl iodide are slowly added. Stirring is continued for 16 hours at which point water (300 ml) is added and the reaction mixture is extracted with ether (3×300 ml). The organic phase is washed with a saturated sodium bicarbonate solution and then with a saturated sodium chloride solution. The reaction mixture is dried on MgSO4, filtered and the solvents are evaporated. The residue is purified by chromatography on a silica column, eluted by a 20/80 mixture of dichloromethane and hexane, yielding 9 g (92% yield) of 4-bromo-2-(1-methylcyclohexyl) anisole in the form of a colorless oil.

Workup

stirringStirring
additionis added
extractionthe reaction mixture is extracted with ether (3×300 ml)
washThe organic phase is washed with a saturated sodium bicarbonate solution
customThe reaction mixture is dried on MgSO4
filtrationfiltered
customthe solvents are evaporated
customThe residue is purified by chromatography on a silica column
washeluted by a 20/80 mixture of dichloromethane and hexane

Sources & evidence

ORD record: ord-baff78d05e044ecc9de376b58d26dd37
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04927928

Reaction notes

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