Congressane → 4,9-Dibromodiamantane

HRID 374077

반응식

HRID 374077 반응식
[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

참가 물질

4

반응물 2

HCID 123154CongressaneHCID 166749Bromhydrol

생성물 1

HCID 130222904,9-Dibromodiamantane수율 650.1%

시약·촉매·용매 1

HCID 24408Bromine용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3fcb860f53e645f6a4374ab41aae2df4
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166313

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