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1,2-Dibromobenzene → 2'-Bromobiphenyl-3-carboxylic acid ethyl ester

HRID 269522
Notes
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Reaction equation

HRID 269522 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)=[O:13])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.C(OCC)(=O)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>[CH2:9]([O:11][C:12]([C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[Br:8])[CH:17]=[CH:16][CH:15]=1)=[O:13])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 3249312(3-Ethoxycarbonylphenyl)boronic acid

Product 1

HCID 587309812'-Bromobiphenyl-3-carboxylic acid ethyl esterYield 67.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent
HCID 882672-Methylphenethyl alcoholSolvent

Procedure

A mixture of 1,2-dibromobenzene (0.63 ml, 5.2 mmol), (3-ethoxycarbonylphenyl)boronic acid (506 mg, 2.6 mmol), tetrakis(triphenylphosphine)palladium(0) (640 mg, 0.6 mmol) and potassium carbonate (2.879 g, 20.9 mmol) was heated in toluene-ethanol (1:1, 10 ml at 90° C. for 3 hours. Upon cooling, the mixture was diluted with ethyl acetate and water. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography using Biotage with iso-hexane containing a gradient of DCM (2-15%) to yield the title compound (538 mg, 34%).

Workup

  1. temperatureUpon cooling
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-f00d8cdedfc244c2b1157fa02a493e53
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446222B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes