Bromobenzene → HCID 66797773, compound

HRID 2275959Notes

Reaction equation

HRID 2275959 reaction equation
[CH3:1][C:2]1([CH3:42])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][C:17]([C:22]1[CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:35])[CH:29]=2)[CH:25]=[CH:26][CH:27]=1)=[CH:16][CH:15]=4.Br[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]1([CH3:42])[C:10]2=[CH:11][C:12]3[N:13]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][C:17]([C:22]1[CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:35])[CH:29]=2)[CH:25]=[CH:26][CH:27]=1)=[CH:16][CH:15]=4

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 66798029HCID 66798029, compound

Product 1

HCID 66797773HCID 66797773, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

9.6 g (17.9 mmol) of [3′-(12,12-dimethyl-10,12-dihydro-10-azaindeno-[2,1-b]fluoren-7-yl)biphenyl-3-yl]phenylmethanone are dissolved in 300 ml of toluene with 3.14 g (20 mmol) of bromobenzene and degassed. 1.9 ml of tri-tert-butylphosphine solution (1 M in toluene), 214 mg (0.94 mmol) of Pd(OAc)2 and 5.4 g (56.7 mmol) of NaOtBu are added, and the mixture is stirred under reflux for 7 h. The warm (45° C.) mixture is filtered through Alox B, washed with water, dried and evaporated. The crude product is extracted with toluene in a Soxhlet extractor and recrystallised from toluene/heptane, giving 7.4 g (12.1 mmol, 60%) of the product as a white solid. Finally, the product is sublimed in a high vacuum, the purity is 99.9%.

Workup

  1. customdegassed
  2. temperatureunder reflux for 7 h
  3. filtrationis filtered through Alox B
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. extractionThe crude product is extracted with toluene in a Soxhlet extractor
  8. customrecrystallised from toluene/heptane

Sources & evidence

ORD record
ord-d8a4c81f8f074c05884149382398f8ef
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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