1,3-Dibromobenzene → 3,3',5,5'-Tetramethyl-7,7'-bis(3,5-dibromophenyl)-1,1'-biadamantane

HRID 41287

Reaction equation

HRID 41287 reaction equation
Br[C:2]12[CH2:24][C:6]3([CH3:25])[CH2:7][C:8]([C:11]45[CH2:21][C:15]6([CH3:22])[CH2:16][C:17](Br)([CH2:19][C:13]([CH3:23])([CH2:14]6)[CH2:12]4)[CH2:18]5)([CH2:10][C:4]([CH3:26])([CH2:5]3)[CH2:3]1)[CH2:9]2.Br[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=1.[Br-:35].[Al+3].[Br-:37].[Br-:38]>Cl>[Br:35][C:2]1[CH:3]=[C:4]([C:2]23[CH2:3][C:4]4([CH3:26])[CH2:10][C:8]([C:11]56[CH2:21][C:15]7([CH3:22])[CH2:16][C:17]([C:28]8[CH:33]=[C:32]([Br:38])[CH:31]=[C:30]([Br:34])[CH:29]=8)([CH2:19][C:13]([CH3:23])([CH2:14]7)[CH2:12]5)[CH2:18]6)([CH2:7][C:6]([CH3:25])([CH2:5]4)[CH2:24]2)[CH2:9]3)[CH:5]=[C:6]([Br:37])[CH:24]=1

Participants

5

Reactant 3

HCID 79271,3-DibromobenzeneHCID 166749BromhydrolHCID 579347073,3'-Dibromo-5,5',7,7'-tetramethyl-1,1'-biadamantane

Product 1

HCID 575583803,3',5,5'-Tetramethyl-7,7'-bis(3,5-dibromophenyl)-1,1'-biadamantaneYield 180%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A 3-liter recovery flask was charged with the above synthesized 7,7′-dibromo-3,3′,5,5′-tetramethyl-1,1′-biadamantane 48.4 g (100 mmol), 1,3-dibromo benzene 1180 g (500 mmol), and a stirrer. While stirring under a nitrogen flow at room temperature, aluminum bromide (III) 26.7 g (100 mmol) was added little by little. After the end of addition, the solution was stirred at 50° C. for 7 hours. The reaction solution was charged into a 1 mol/liter hydrochloric acid solution 2 liter, the aqueous phase was removed by separation, then acetone 1 liter was added for extraction. The solid was collected by filtration and dried under reduced pressure to obtain 7,7′-bis(3,5-dibromophenyl)-3,3′,5,5′-tetramethyl-1,1′-biadamantane (90.0 mmol; yield 90.0%) 71.5 g.

Workup

  1. additionA 3-liter recovery flask was charged with the
  2. additionAfter the end of addition
  3. stirringthe solution was stirred at 50° C. for 7 hours
  4. customthe aqueous phase was removed by separation
  5. additionacetone 1 liter was added for extraction
  6. filtrationThe solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-482d535ef50f4cb0ae074e5269c7e9b0
Source dataset
uspto-grants-2013_09
Patent number
US08530596B2

Linked notes

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