Water → 1-(5-Bromo-2-methoxyphenyl)adamantane

HRID 1491507Notes

Reaction equation

HRID 1491507 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:21]I.O>C1COCC1>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH3:21])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46704942-(1-Adamantyl)-4-bromophenol

Product 1

HCID 32850241-(5-Bromo-2-methoxyphenyl)adamantane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of sodium hydride (80% in oil, 4.32 g, 144 mmol) in 50 ml of THF, there are slowly added, while maintaining the temperature at 20° C., 36.8 g (120 mmol) of 2-(1-adamantyl)-4-bromophenol. The mixture is stirred for 1 hour at ambient temperature at which point 9 ml (144 mmol) of methyl iodide are added. The mixture is then stirred for 2 hours at 20° C., poured into water, extracted with ether, dried and evaporated. The product is purified by passage through a silica column (10×30 cm), eluting with a mixture of hexane (90%) and dichloromethane (10%). On evaporation, 26.2 g of a white solid are obtained. Yield - 68%. Melting point: 138°-139° C.

Workup

  1. additionare slowly added
  2. additionare added
  3. extractionextracted with ether
  4. customdried
  5. customevaporated
  6. customThe product is purified by passage through a silica column (10×30 cm)
  7. washeluting with a mixture of hexane (90%) and dichloromethane (10%)
  8. customOn evaporation, 26.2 g of a white solid
  9. customare obtained
  10. customYield - 68%

Sources & evidence

ORD record
ord-9e01c09f154f494896bc9c5d78f1ab18
Source dataset
uspto-grants-1994_12
Patent number
USRE034805

Reaction notes

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