Potassium Carbonate → 2'-Bromo-5-chloro-2-[(phenylmethyl)oxy]biphenyl

HRID 269567Notes

Reaction equation

HRID 269567 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:14](I)[CH:13]=1.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:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]1[CH:13]=[C:12]([Cl:11])[CH:17]=[CH:16][C:15]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2773294(2-Bromophenyl)boronic acid2×HCID 21112926Benzene, 4-chloro-2-iodo-1-(phenylmethoxy)-HCID 21863594Toluene ethanol

Product 1

HCID 693094132'-Bromo-5-chloro-2-[(phenylmethyl)oxy]biphenylYield 55.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 21584184Diethylether waterSolvent

Procedure

A mixture of 2-bromophenylboronic acid (2.01 g, 10 mmol), 4-chloro-2-iodo-1-[(phenylmethyl)oxy]benzene (3.445 g, 10 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (580 mg, 0.5 mmol) in 1:1 toluene/ethanol (45 ml) was stirred and heated at 90° C. under nitrogen for 2 hours when a further 1 g (4.98 mmol) of 2-bromophenylboronic acid and 0.2 g (0.17 mmol) of tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated for 6 hours then cooled, diluted with diethyl ether/water and the organic phase separated, dried (magnesium sulphate) and evaporated. The residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:49) then rechromatographed eluting with dichloromethane/iso-hexane (1:9) to give 2.06 g of colourless gum which slowly crystallised.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated for 6 hours
  3. temperaturethen cooled
  4. customthe organic phase separated
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customThe residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:49)
  8. customthen rechromatographed
  9. washeluting with dichloromethane/iso-hexane (1:9)

Sources & evidence

ORD record
ord-dec43baa2d1b42faafbfaad440a7600e
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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