Hydrochloric Acid → 1,4-Bis(4-di(4-bromophenyl)aminostyryl)benzene

HRID 1190240Notes

Reaction equation

HRID 1190240 reaction equation
C(OP(=O)O[CH2:6][CH3:7])C.[C:9]1([CH3:16])[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[Na+].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)[C:31]2[CH:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][CH:32]=2)=[CH:26][CH:25]=1.Cl>CN(C=O)C.C(O)C>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]([C:7]2[CH:6]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)[C:31]2[CH:32]=[CH:21][C:18]([CH:19]=[CH:16][C:9]3[CH:14]=[CH:13][C:12]([CH:15]=[CH:37][C:34]4[CH:35]=[CH:36][C:31]([N:30]([C:39]5[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=5)[C:27]5[CH:28]=[CH:29][C:24]([Br:23])=[CH:25][CH:26]=5)=[CH:32][CH:33]=4)=[CH:11][CH:10]=3)=[CH:17][CH:36]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 186689044-(Bis(4-bromophenyl)amino)benzaldehydeHCID 23676156Sodium t-butoxideHCID 178476836HCID 178476836, compound

Product 1

HCID 765979301,4-Bis(4-di(4-bromophenyl)aminostyryl)benzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 37.8 g (100 mmol) of p-xylene diethylphosphonate in 200 ml of DMF is added to a suspension, cooled to 0° C., of 38.5 g (400 mmol) of sodium tert-butoxide in 1000 ml of anhydrous DMF. After the mixture has been stirred for a further 30 min., a solution of 90.5 g (210 mmol) of bis(4-bromophenyl)(4-formylphenyl)amine in 300 ml of DMF is added over the course of 30 min., the mixture is stirred at 0° C. for a further 4 h, and then 500 ml of 1N hydrochloric acid and 300 ml of ethanol are added. The solid is filtered off with suction, washed three times with 300 ml of water and three times with 200 ml of ethanol and dried under reduced pressure. The product is subsequently recrystallised from DMF, filtered off with suction, washed three times with 200 ml of ethanol and dried under reduced pressure. Yield: 86.1 g (92 mmol), 92.3% of theory; purity: 99% according to 1H-NMR.

Workup

  1. stirringthe mixture is stirred at 0° C. for a further 4 h
  2. filtrationThe solid is filtered off with suction
  3. washwashed three times with 300 ml of water and three times with 200 ml of ethanol
  4. customdried under reduced pressure
  5. customThe product is subsequently recrystallised from DMF
  6. filtrationfiltered off with suction
  7. washwashed three times with 200 ml of ethanol
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ec032bfb0c0e4e57804ee32111196472
Source dataset
uspto-grants-2014_03
Patent number
US08674141B2

Reaction notes

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