1,2-Dibromobenzene → 2'-Bromo-biphenyl-3-carbonitrile

HRID 269539Notes

Reaction equation

HRID 269539 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1Br.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:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

7

Reactant 3

HCID 114141,2-DibromobenzeneHCID 27343253-Cyanophenylboronic acidHCID 21863594Toluene ethanol

Product 1

HCID 13924952'-Bromo-biphenyl-3-carbonitrileYield 69.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-cyanophenylboronic acid (735 mg, 5 mmol), 1,2-dibromobenzene (2.36 g, 10 mmol) potassium carbonate (6.9 g, 50 mmol) and tetrakis(triphenylphosphine)palladium(0) (580 mg, 0.5 mmol) in 1:1 toluene/ethanol (40 ml) was stirred and heated at 90° C. under nitrogen for 3 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 ethyl acetate/iso-hexane (1:19) to yield the title compound as a white solid (895 mg 69%).

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-61ef2a173c7c443d8121534960b66168
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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