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

HRID 1734784Notes

Reaction equation

HRID 1734784 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-bromophenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6.92 g (40.0 mmol) of 4-bromophenol and 6.08 g (40.0 mmol) of 1-adamantanol in 20 ml of dichloromethane (anhydrous) was added 2.0 ml of conc. sulfuric acid over a span of 2 minutes. The solution became orange in color and a white precipitate was formed. The solution was allowed to stir at room temperature for 8 hours, partitioned between 250 ml of water and 100 ml of ethyl ether, diluted with approximately 60 ml of sat. aqueous NaHCO3 solution and allowed to stir at room temperature. The layers were separated and the aqueous phase was washed with 3×75 ml-portions of dichloromethane. All organic phases were combined, dried over MgSO4, filtered and concentrated in vacuo to yield a yellow solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a light yellow solid. PMR (CDCl3):d 1.77 (6H, s), 2.08 (9H, s), 4.76 (1H, s), 6.53 (1H, d, J=8.4 Hz), 7.14 (1H, dd, J=8.4, 2.4 Hz), 7.29 (1H, d, J=2.4 Hz).

Workup

  1. customa white precipitate was formed
  2. custompartitioned between 250 ml of water and 100 ml of ethyl ether
  3. additiondiluted with approximately 60 ml of sat. aqueous NaHCO3 solution
  4. stirringto stir at room temperature
  5. customThe layers were separated
  6. washthe aqueous phase was washed with 3×75 ml-portions of dichloromethane
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a yellow solid
  11. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bf4ca9ce1ea34470883e5ccf47faed29
Source dataset
uspto-grants-1996_07
Patent number
US05534641

Reaction notes

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