Triphenylphosphine → HCID 11831969, compound

HRID 1379163Notes

Reaction equation

HRID 1379163 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13].[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=CC=C[CH:17]=1.B(O)O>C1(C)C=CC=CC=1.O.CCO.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:16]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13])([CH3:21])=[CH2:17]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 61668Boronic AcidHCID 11109119methyl 3-methylsulfonyl-4-bromobenzoate

Product 1

HCID 11831969HCID 11831969, compoundYield 189.8%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

23 mmol of methyl 4-bromo-3-methylsulfonylbenzoate, 54 mmol of Na2 CO3, 2.9 mmol of triphenylphosphine and 1.5 mmol of Pd(OAc)2 are stirred intensively at RT for 5 min in 200 ml of toluene and 15 ml of H2O. A solution of 23 mmol of boronic acid according to Preliminary Stage 1 is then added in 50 ml of EtOH and the mixture is boiled under reflux for 1.5 h. After phase separation, the organic phase is washed twice with 50 ml of NaCl solution and the aqueous phase is extracted twice with 100 ml of EA. The combined organic phases are dried over Na2 SO4, the solvents are removed in vacuo and the residue is chromatographed on silica gel using DIP. 1.4 g of a colorless oil are obtained.

Workup

  1. temperatureunder reflux for 1.5 h
  2. customAfter phase separation
  3. washthe organic phase is washed twice with 50 ml of NaCl solution
  4. extractionthe aqueous phase is extracted twice with 100 ml of EA
  5. customThe combined organic phases are dried over Na2 SO4
  6. customthe solvents are removed in vacuo
  7. customthe residue is chromatographed on silica gel using DIP

Sources & evidence

ORD record
ord-258fe0d96082498e8fb18c9246390b73
Source dataset
uspto-grants-1997_09
Patent number
US05670544

Reaction notes

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