Toluene → 2'-Benzyloxy-2-bromobiphenyl

HRID 269534

Reaction equation

HRID 269534 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br.C1(C)C=CC=CC=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.O.C(OCC)C.C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acid

Product 1

HCID 587309892'-Benzyloxy-2-bromobiphenylYield 69.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-benzyloxyphenylboronic acid (4.3 g. 19.3 mmol) and 1,2-dibromobenzene (9.11 g, 4.66 ml, 38.6 mmol) in 1:1 toluene:ethanol (150 ml) was stirred under nitrogen and tetrakis(triphenylphosphine)palladium(0) (1.12 g, 0.95 mmol) and potassium carbonate (21.3 g, 154 mmol) added. The reaction was stirred at 90° C. under nitrogen for 2 hours. After cooling, diethyl ether (100 ml) and water (100 ml) were added and the organic phase separated. The aqueous phase was extracted with diethyl ether (50 ml) and the combined organic layers washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed (silica gel, 5-15% CH2Cl2-isohexane) to give the title compound as a clear oil (4.53 g, 69%).

Workup

  1. temperatureAfter cooling
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with diethyl ether (50 ml)
  4. washthe combined organic layers washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customchromatographed (silica gel, 5-15% CH2Cl2-isohexane)

Sources & evidence

ORD record
ord-09e66ee2f0534b5281064bf3de981d67
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

Loading…