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

HRID 860525Notes

Reaction equation

HRID 860525 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([Br:10])=[CH:4][C:3]=2[O:2]1.[C:11]12(O)[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.S(=O)(=O)(O)O>C(Cl)Cl>[C:11]12([C:7]3[CH:6]=[C:5]([Br:10])[CH:4]=[C:3]4[O:2][CH2:1][O:9][C:8]=34)[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 641521-AdamantanolHCID 758311-Bromo-3,4-(methylenedioxy)benzene

Product 1

HCID 194297023-(1-Adamantyl)-4,5-methylenedioxybromobenzeneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3,4-methylenedioxy-1-bromobenzene (5.00 g, 24.87 mmol) and 1-adamantanol (3.79 g, 24.87 mmol) in CH2Cl2 (50 mL) under an atmosphere of argon was added sulfuric acid (2.0 mL) at room temperature. After stirring for 3 days the resulting mixture was diluted with CH2Cl2 and washed with water. The aqueous layer was extracted with CH2Cl2 and the combined organics were washed successively with water, brine and dried (MgSO4). The mixture was filter, evaporated and the residue purified on silica gel (hexane) to give 4.41 g of 3-(1-adamantyl)-4,5-methylenedioxy-1-bromobenzene (53%) as a white solid, mp 135.5–136.0° C.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organics were washed successively with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe mixture was filter
  6. customevaporated
  7. customthe residue purified on silica gel (hexane)

Sources & evidence

ORD record
ord-312b7ff68e784fd3b3f3eecd0fc688b7
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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