Reaction #1239

Reaction equation

tert-butyldimethylsilyl chloride

7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene

DMF

triethylamine

→

7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with ethyl ether
2. 2
   Otherthe organic phase decanted
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Otherevaporated
5. 5
   OtherThe residue obtained
6. 6
   Otherwas purified by chromatography on a silica column
7. 7
   Washeluted with heptane
8. 8
   Other12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered

Procedure

11.9 g (33.3 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene, 120 ml of DMF, 5.1 ml (36.6 mmol) of triethylamine and 203 mg of 4-dimethylaminopyridine were introduced successively into a three-necked flask. A solution of 5.52 g (36.6 mmol) of tert-butyldimethylsilyl chloride was added dropwise and the mixture was stirred at room temperature for 12 hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with heptane; 12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered.

Source