Sulfuric Acid → 1-(5-Bromo-2-methoxyphenyl)adamantane

HRID 733653Notes

Reaction equation

HRID 733653 reaction equation
OS(O)(=O)=O.[CH2:6]1[CH:11]2[CH2:12][C:13]3(O)[CH2:15][CH:9]([CH2:10]2)[CH2:8][CH:7]1[CH2:14]3.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>C(Cl)Cl>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[C:22]([C:13]23[CH2:14][CH:7]4[CH2:8][CH:9]([CH2:10][CH:11]([CH2:6]4)[CH2:12]2)[CH2:15]3)[CH:23]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 77304-BromoanisoleHCID 641521-Adamantanol

Product 1

HCID 32850241-(5-Bromo-2-methoxyphenyl)adamantaneYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reagent grade concentrated H2SO4 (11 mL) was added dropwise to a solution of 1-adamantol (30.25 g, 200 mmol) and 4-bromoanisole (37.21 g, 200 mmol) in 130 mL of CH2Cl2. The light pink solution was stirred at ambient temperature for 20 hours. The solvent was decanted, water (100 mL) and hexane (100 mL) were added and the solid was filtered and washed with hexane and dried to give 31 g of the product as a white powder. The supernatant was diluted with hexane, washed with water and brine, dried over MgSO4 and filtered thru a silica gel pad. The solvent was removed and the solid was recrystallized from hexane to yield 17 g of the product as a white powder.

Workup

  1. customThe solvent was decanted
  2. additionwater (100 mL) and hexane (100 mL) were added
  3. filtrationthe solid was filtered
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-caa20734bbd0400b9f7b251df1176d57
Source dataset
uspto-grants-2009_09
Patent number
US07589239B2

Reaction notes

Loading…