1,2-Dibromobenzene → HCID 69310719, compound

HRID 269526

Reaction equation

HRID 269526 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=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>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[Br:15])[CH:3]=[C:2]([NH2:1])[CH:7]=1)=[O:9]

Participants

8

Reactant 4

HCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 2737799(3-Amino-5-(methoxycarbonyl)phenyl)boronic acidHCID 21863594Toluene ethanol

Product 1

HCID 69310719HCID 69310719, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (3-amino-5-methoxycarbonylphenyl)boronic acid (1.02 g, 5.23 mmol), 1,2-dibromobenzene (2.47 g, 10.46 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (606 mg, 0.523 mmol) in 1:1 toluene/ethanol (30 ml) was stirred and heated at 90° C. under nitrogen for 2 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 using Biotage with ethyl acetate/iso-hexane (3:17) to yield the title compound as a colourless gum (1.21 g, 76%).

Workup

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

Sources & evidence

ORD record
ord-c184d1913744492f993b42022b19c865
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

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