1,3-Dibromobenzene → HCID 59866480, compound

HRID 2039429Notes

Reaction equation

HRID 2039429 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.O>[Br:17][C:18]1[CH:19]=[C:20]([C:4]2[C:5]3[S:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

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

Product 1

HCID 59866480HCID 59866480, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Dibenzo[b,d]thiophen-4-yl-boronic acid (10.00 g, 43.8 mmol), 1,3-dibromobenzene (20.69 g, 88 mmol) and Pd(PPh3)4 catalyst (0.507 g, 0.438 mmol) were dissolved in 200 mL of toluene, and potassium carbonate (18.18 g, 132 mmol) in 50 mL of water was added, and the mixture was refluxed overnight under N2. The mixture was cooled to room temperature, and the organic layer was separated, filtered and evaporated. The residue after evaporation was purified by column chromatography on silica gel (eluted with hexane/DCM 95/5 v/v mixture), followed by recrystallization from hexane. 4-(3-bromophenyl)dibenzo[b,d]thiophene was obtained as white solid (12 g, 81% yield).

Workup

  1. temperaturethe mixture was refluxed overnight under N2
  2. customthe organic layer was separated
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue after evaporation
  6. customwas purified by column chromatography on silica gel (eluted with hexane/DCM 95/5 v/v mixture)
  7. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-370799ebaa9d4434b92425a9dfeb29c4
Source dataset
uspto-grants-2013_11
Patent number
US08580399B2

Reaction notes

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