Dichloromethane → HCID 68337306, compound

HRID 1529519Notes

Reaction equation

HRID 1529519 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([N:19]3[C:38]4[C:26](=[CH:27][C:28]5[C:29]([CH3:46])([CH3:45])[C:30]6[CH:31]=[C:32]([C:39]7[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=7)[CH:33]=[CH:34][C:35]=6[C:36]=5[CH:37]=4)[C:25]4[C:20]3=[CH:21][CH:22]=[C:23](B(O)O)[CH:24]=4)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.ClCCl>O.O1CCOCC1.C1(C)C=CC=CC=1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([N:19]3[C:38]4[C:26](=[CH:27][C:28]5[C:29]([CH3:46])([CH3:45])[C:30]6[CH:31]=[C:32]([C:39]7[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=7)[CH:33]=[CH:34][C:35]=6[C:36]=5[CH:37]=4)[C:25]4[C:20]3=[CH:21][CH:22]=[C:23]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:24]=4)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 6344DichloromethaneHCID 7961BromobenzeneHCID 67151755HCID 67151755, compound

Product 1

HCID 68337306HCID 68337306, compound

Reagents, catalysts & solvents 4

HCID 178420553HCID 178420553, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

26.6 g (42 mmol) of 6-(4,6-diphenylpyrimidin-2-yl)-12,12-dimethyl-2-phenyl-6,12-dihydro-6-azaindeno[1,2-b]fluorene-9-boronic acid and 8.2 g (52.4 mmol) of bromobenzene are dissolved in a degassed mixture of 135 ml of water, 315 ml of dioxane and 315 ml of toluene, and 5.33 g (50.31 mmol) of Na2 CO3 are added. The reaction mixture is degassed, and 0.96 g (0.84 mmol) of tetrakistriphenylphosphinopalladium(0) is added. The mixture is heated under reflux for 18 h. After cooling, dichloromethane is added (heterogeneous mixture), the water phase is separated off, and the organic phase is evaporated azeotropically with toluene. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum. The purity is 99.9%, the yield is 23 g (34 mmol, 82%).

Workup

  1. additionare added
  2. customThe reaction mixture is degassed
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 18 h
  5. temperatureAfter cooling
  6. customthe water phase is separated off
  7. customthe organic phase is evaporated azeotropically with toluene
  8. extractionThe residue is extracted with hot toluene
  9. customrecrystallised from toluene

Sources & evidence

ORD record
ord-aa7d7081c8e44475bc20a10d69587c8b
Source dataset
uspto-grants-2015_07
Patent number
US09090590B2

Reaction notes

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