Congressane → 4,9-Dibromodiamantane

HRID 374077

Reaction equation

HRID 374077 reaction equation
[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

Participants

4

Reactant 2

HCID 123154CongressaneHCID 166749Bromhydrol

Product 1

HCID 130222904,9-DibromodiamantaneYield 650.1%

Reagents, catalysts & solvents 1

HCID 24408BromineSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3fcb860f53e645f6a4374ab41aae2df4
Source dataset
uspto-grants-1992_11
Patent number
US05166313

Linked notes

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