Sulfuric Acid → 3-(1-Adamantyl)-4,5-methylenedioxybromobenzene

HRID 1078515Notes

Reaction equation

HRID 1078515 reaction equation
C(O[C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)(=O)C.S(=O)(=O)(O)O.[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([Br:29])=[CH:23][C:22]=2[O:21]1.C(=O)(O)[O-].[Na+]>C1CCCCC1.CCCCCCC.O>[C:5]12([C:26]3[CH:25]=[C:24]([Br:29])[CH:23]=[C:22]4[O:21][CH2:20][O:28][C:27]=34)[CH2:6][CH:7]3[CH2:13][CH:11]([CH2:10][CH:9]([CH2:8]3)[CH2:14]1)[CH2:12]2

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 516892Sodium BicarbonateHCID 5199731-Adamantyl acetate

Product 1

HCID 194297023-(1-Adamantyl)-4,5-methylenedioxybromobenzene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8078CyclohexaneSolventHCID 8900HeptaneSolvent

Procedure

4.82 g (24.9 mmol) of acetoxyadamantane and 0.75 ml (139 mmol) of concentrated sulphuric acid are added to 5 g (24.9 mmol) of 3,4-methylenedioxybromobenzene in 35 ml of cyclohexane and 35 ml of heptane. The reaction medium is stirred at room temperature overnight. This medium is then hydrolyzed with 250 ml of water, neutralized with sodium bicarbonate, extracted with 200 ml of dichloromethane, dried over magnesium sulphate and evaporated, to give 2.89 g (34.8%) of the expected derivative which melts at 134° C.)

Workup

  1. extractionextracted with 200 ml of dichloromethane
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. customto give 2.89 g (34.8%) of the expected derivative which melts at 134° C.)

Sources & evidence

ORD record
ord-c094ee2e80b94504a44171caaf46df4d
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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