Potassium Carbonate → HCID 66798006, compound

HRID 2275943Notes

Reaction equation

HRID 2275943 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)([O-:17])=[O:16].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([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)=CC=1>[N+:15]([C:18]1[CH:19]=[C:20]([C:2]2[CH:14]=[CH:13][C:5]3[S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:4]=3[CH:3]=2)[CH:21]=[CH:22][CH:23]=1)([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2995082-BromodibenzothiopheneHCID 2773548(2-Nitrophenyl)boronic acid

Product 1

HCID 66798006HCID 66798006, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

15.0 g of 2-bromodibenzothiophene (57.0 mmol) and 14.3 g of 2-nitrophenylboronic acid (85.5 mmol) are dissolved in 400 ml of toluene and degassed. 370 ml of a degassed 2 M K2CO3 and 1.6 g of Pd(PPh3)4 (1.4 mmol) are added. The reaction mixture is stirred at 80° C. for 48 h under a protective-gas atmosphere. Further toluene is added to the cooled solution, which is washed a number of times with water, dried and evaporated. The residue in the form of a yellowish oil is employed in the subsequent reaction without further purification. The yield is 16.9 g (55.4 mmol, 89%).

Workup

  1. customdegassed
  2. washis washed a number of times with water
  3. customdried
  4. customevaporated
  5. customThe residue in the form of a yellowish oil is employed in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-77c83315d78c47ababd2de56e228b7bd
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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