1,2-Dibromobenzene → HCID 46867078, compound

HRID 269524Notes

Reaction equation

HRID 269524 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1Br.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.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:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Participants

8

Reactant 4

HCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 21863594Toluene ethanol

Product 1

HCID 46867078HCID 46867078, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-acetylphenylboronic acid (1.64 g, 10 mmol), 1,2-dibromobenzene (4.72 g, 20 mmol), potassium carbonate (6.9 g, 50 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.5 mmol) in 1:1 toluene/ethanol (40 ml) was stirred and heated at 90° C. under nitrogen for 16 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography using Biotage with iso-hexane containing a gradient of dichloromethane (20-50%) to yield the title compound as a white solid (1.74 g 63%).

Workup

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-70c133058d284e82a4e3505a53d897a5
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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