Sulfuric Acid → 2-(1-Adamantyl)-4-bromophenol

HRID 2110395Notes

Reaction equation

HRID 2110395 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]12(O)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.S(=O)(=O)(O)O>ClCCl>[C:9]12([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[OH:8])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 78084-BromophenolHCID 641521-Adamantanol

Product 1

HCID 46704942-(1-Adamantyl)-4-bromophenolYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

51.9 g (300 mmol) of 4-bromophenol and 45.7 g (300 mmol) of adamantan-1-ol are dissolved in 150 ml of dichloromethane; 15 ml of 98% sulfuric acid are slowly run in and the reaction medium is stirred at ambient temperature for two days. The medium is evaporated to dryness, taken up with water, neutralized to pH=7-8, filtered, taken up in THF, dried over MgSO4, evaporated, and purified on a silica column, elution being carried out with a 10/90 ether/heptane mixture. A thick oil is obtained (m=58 g, yield=63%).

Workup

  1. customThe medium is evaporated to dryness
  2. filtrationfiltered
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. custompurified on a silica column, elution
  6. customA thick oil is obtained (m=58 g, yield=63%)

Sources & evidence

ORD record
ord-20b3ac33aba5440ba335f9f7b81aa413
Source dataset
uspto-grants-2009_04
Patent number
US07517907B2

Reaction notes

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