Congressane → 4,9-Dibromodiamantane

HRID 374077

反応式

HRID 374077 の反応式
[CH2:1]1[CH:6]2[CH:7]3[CH:13]4[CH2:14][CH:2]1[CH2:3][CH:4]1[CH:12]4[CH2:11][CH:9]([CH2:10][CH:5]12)[CH2:8]3.[Br-:15].[Al+3].[Br-:17].[Br-]>BrBr>[CH2:14]1[C:2]2([Br:15])[CH2:1][CH:6]3[CH:5]4[CH2:10][C:9]5([Br:17])[CH2:11][CH:12]([CH:4]4[CH2:3]2)[CH:13]1[CH:7]3[CH2:8]5

参加物

4

反応物 2

HCID 123154CongressaneHCID 166749Bromhydrol

生成物 1

HCID 130222904,9-Dibromodiamantane収率 650.1%

試薬・触媒・溶媒 1

HCID 24408Bromine溶媒

反応条件

温度
0 °C

実験手順

Diamantane (50 g, 0.26 mol) was added over 1 h to bromine (200 mL) at 0° C. Aluminum bromide (5.4 g, 0.02 mol) was added and the mixture was stirred at 0° C. for 3 h and at ambient temperature for 16 h. When glc showed less than 5% monobrominated diamantanes, the bromine was removed under reduced pressure and the residue was triturated with pentane (300 mL). The precipitate was filtered, and was washed with pentane (2×150 mL) and methanol (3×100 mL). The residue was recrystallized from toluene to give 45 g (50%) of 4,9-dibromodiamantane, a white solid: mp 328° C. (lit. mp 324°-326° C.); 1H NMR (CDCl3) δ1.97 (s, 6H) 2.31 (s, 12H); 13C NMR (CDCl3) δ39.64, 48.45, 62.81.

後処理

  1. customthe bromine was removed under reduced pressure
  2. customthe residue was triturated with pentane (300 mL)
  3. filtrationThe precipitate was filtered
  4. washwas washed with pentane (2×150 mL) and methanol (3×100 mL)
  5. customThe residue was recrystallized from toluene

出典と根拠

ORDレコード
ord-3fcb860f53e645f6a4374ab41aae2df4
出典データセット
uspto-grants-1992_11
特許番号
US05166313

関連ノート

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