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

HRID 860525

반응식

HRID 860525 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-312b7ff68e784fd3b3f3eecd0fc688b7
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153875B2

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