Water → 2-Bromo-3',4,4',5-tetrakis(2-methylbutoxy)-1,1'-biphenyl

HRID 1182322Notes

Reaction equation

HRID 1182322 reaction equation
[CH3:1][CH:2]([CH2:35][CH3:36])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]([CH3:28])[CH2:26][CH3:27])=[C:19]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[CH:18]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15].[Br:37]N1C(=O)CCC1=O.O>C(OCC)(=O)C>[Br:37][C:22]1[CH:21]=[C:20]([O:23][CH2:24][CH:25]([CH3:28])[CH2:26][CH3:27])[C:19]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])=[CH:18][C:17]=1[C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15])=[C:5]([O:4][CH2:3][CH:2]([CH3:1])[CH2:35][CH3:36])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 17938208HCID 17938208, compound

Product 1

HCID 179382092-Bromo-3',4,4',5-tetrakis(2-methylbutoxy)-1,1'-biphenylYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
2.5 °C

Procedure

339 g (679.7) mmol of 3,3′,4,4′-tetra(2-methylbutyloxy)biphenyl were dissolved in 800 ml of ethyl acetate. 120.98 g (679.7 mmol) of N-bromosuccinimide were then added in solid form over a period of 15 minutes under protective gas, in the absence of light and with cooling to 0-5° C. The suspension was slowly warmed to room temperature under a blanket of protective gas and was then stirred vigorously at room temperature for 4 hours. 500 ml of ethyl acetate and 300 ml of water were added, the phases were separated and the aqueous phase was extracted twice with 100 ml each time of ethyl acetate. The combined organic phases were washed twice with 50 ml each time of water and dried over MgSO4. The oil obtained was filtered through silica gel with the aid of hexane. Taking off the solvent gave 361.2 g (625.3 mmol, 92%) of 2-bromo-4,5,3′,4′-tetra(2-methylbutyloxy)biphenyl as a colorless oil.

Workup

  1. temperatureThe suspension was slowly warmed to room temperature under a blanket of protective gas
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted twice with 100 ml each time of ethyl acetate
  4. washThe combined organic phases were washed twice with 50 ml each time of water
  5. dry with materialdried over MgSO4
  6. customThe oil obtained
  7. filtrationwas filtered through silica gel with the aid of hexane

Sources & evidence

ORD record
ord-2835ee994f5546c2898283b8dad51866
Source dataset
uspto-grants-2007_10
Patent number
US07288617B2

Reaction notes

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