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

HRID 2377221Notes

Reaction equation

HRID 2377221 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-831a458fe2f64af5bf45221c0d7b6d21
Source dataset
uspto-grants-2008_12
Patent number
US07468462B2

Reaction notes

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