Toluene → HCID 59866480, compound

HRID 1468599Notes

Reaction equation

HRID 1468599 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[S:14][C:13]=2[C:12](B(O)O)=[CH:11][CH:10]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>O.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>[Br:8][C:4]1[CH:3]=[C:2]([C:21]2[C:15]3[S:14][C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:17]=4[C:16]=3[CH:18]=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 2734329Dibenzothiophene-4-boronic acid

Product 1

HCID 59866480HCID 59866480, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A nitrogen flushed mixture of 1,3-dibromobenzene (18.63 g, 78.92 mmol), dibenzo{b,d}thiophen-4-ylboronic acid (6.0 g, 26.3 mmol), Pd(PPh3)4 (304 mg, 0.414 mmol), toluene (200 mL) and a slurry of K2CO3 (10.9 g, 78.92 mmol) in water (20 mL) were refluxed for 23 h. After the mixture cooled to room temperature the organic layer was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by vacuum distillation (Kugelrohr) followed by flash chromatography on silica (hexane:dichloromethane) to give 4-(3-bromophenyl)dibenzo[b,d]thiophene (3.5 g 39.2%).

Workup

  1. customA nitrogen flushed
  2. washwas washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was purified by vacuum distillation (Kugelrohr)

Sources & evidence

ORD record
ord-d4e50c81f9f44b248efccbd870c718b0
Source dataset
uspto-grants-2015_04
Patent number
US09005771B2

Reaction notes

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