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

HRID 860525ノート

反応式

HRID 860525 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-312b7ff68e784fd3b3f3eecd0fc688b7
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

反応ノート

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