Ethanol → 2,8-Diphenyl-dibenzo-thiophene

HRID 1748936Notes

Reaction equation

HRID 1748936 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]3[CH:12]=[CH:11][C:10](Br)=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](O)[CH3:32]>C1(C)C=CC=CC=1.O>[C:16]1([C:2]2[CH:15]=[CH:14][C:5]3[S:6][C:7]4[CH:12]=[CH:11][C:10]([C:32]5[CH:31]=[CH:4][CH:3]=[CH:2][CH:15]=5)=[CH:9][C:8]=4[C:4]=3[CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 6311202,8-Dibromodibenzothiophene

Product 1

HCID 223821962,8-Diphenyl-dibenzo-thiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2,8-dibromo-dibenzo[b,d]thiophene (14 g), phenylboronic acid (11.0 g) tetrakis(triphenylphosphine)palladium (3.8 g) and potassium carbonate (20 g) were refluxed together in a mixture of toluene (110 mL), ethanol (20 mL) and water (90 mL) overnight. The reaction was quenched with water and the toluene layer was removed and passed through a celite column and the toluene layer was evaporated in a rotary evaporator to yield 6.0 g 2,8-diphenyl-dibenzo[b,d]thiophene.

Workup

  1. customThe reaction was quenched with water
  2. customthe toluene layer was removed
  3. customthe toluene layer was evaporated in a rotary evaporator

Sources & evidence

ORD record
ord-3288b2bbd8864151bf05c7a78447c142
Source dataset
uspto-grants-2015_10
Patent number
US09153787B2

Reaction notes

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