Reaktion #595847

Reaktionsgleichung

4-bromo-3-methylphenol

1-adamantanol

MeSO3H

→

2-(1-adamantyl)-4-bromo-5-methylphenol

Ausbeute 85.0%

Lösungsmittel

CH2Cl2

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with H2O, 5% NaHCO3, and brine
2. 2
   Sonstigedried
3. 3
   SonstigeThe residue obtained on concentration
4. 4
   Waschenwas washed with hot hexane

Vorschrift

A mixture of 4-bromo-3-methylphenol (4.68 g, 25 mmol), 1-adamantanol (3.81 g, 25 mmol), and MeSO3H (1.2 mL) in CH2Cl2 (18 mL) was stirred and heated at 54° C. (oil-bath) for 28.8 h. The resulting solution was diluted with CHCl3 (150 mL), washed with H2O, 5% NaHCO3, and brine and dried. The residue obtained on concentration was washed with hot hexane to give 6.77 g (85%) of 2-(1-adamantyl)-4-bromo-5-methylphenol as a white solid, mp 155-156° C. IR 3541, 2905, 2845, 1147 cm−1; 1H NMR δ (CDCl3) 1.77 (bs, 6H, AdCH2), 2.07 (bs, 9H, AdCH and AdCH2), 2.28 (s, 3H, CH3), 4.67 (s, 1H, OH), 6.54 (s, 1H, 6-ArH), 7.30 (s, 1H, 3-ArH).

Quelle