Water → 4-Bromotriphenylamine

HRID 1795725Notes

Reaction equation

HRID 1795725 reaction equation
[Br:1]N1C(=O)CCC1=O.O.[C:10]1([N:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:23]1([N:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:17]2[CH:22]=[CH:21][C:20]([Br:1])=[CH:19][CH:18]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 962WaterHCID 11775TriphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 6428384-BromotriphenylamineYield 60%

Procedure

In addition, 15 g of triphenylamine dissolved in 50 ml of N,N-dimethylformide is prepared. 11.4 g of N-bromosuccinimide is added into the N,N-dimethylformide solution and the solution is stirred for 12 hours. After 20 ml of water is added, a white crystal is obtained. The white crystal is filtered and dried to obtain 11.70 g of N,N-diphenyl-4-bromoaniline (60%). Next, 8.26 g of N,N-diphenyl-4-bromoaniline is dissolved in 100 ml of tetrahydrofuran. After cooling the solution to −78° C., 24 ml of n-butyl lithium is dropt into the cold solution slowly, then the solution is stirred for 2 hours and the temperature of solution is raised to 0° C. Then, the reacting solution is cooled to −78° C. again, and 5.2 ml of boric acid trimethyl ester is added into the solution slowly. After stirring the reacting solution for 12 hours, 20 ml of 2N HCl is added to terminate the reaction. 100 ml of ethyl ether is used to extract the solution, and the extracted solution is dehydrated by MgSO4. Then, the extracted solution is concentrated, and hexane is added to obtain a white crystal. This white crystal is filtered and dried to obtain 4.3 g of compound (B)(60%).

Workup

  1. customis prepared
  2. customa white crystal is obtained
  3. filtrationThe white crystal is filtered
  4. customdried

Sources & evidence

ORD record
ord-d23b4b817e5041f986be341c27205bc2
Source dataset
uspto-grants-2006_04
Patent number
US07029764B2

Reaction notes

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