Citric Acid → HCID 68006223, compound

HRID 1026571Notes

Reaction equation

HRID 1026571 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])O1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.O1CCOCC1>[OH:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 22568915Benzyl 4-bromo-2-methylbenzoate

Product 1

HCID 68006223HCID 68006223, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 1,4-dioxane solution (99 ml) of benzyl 4-bromo-2-methylbenzoate (6.63 g) were added at room temperature 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenol (4.86 ml), tripotassium phosphate hydrate (16.8 g), a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-dichloromethane complex (860 mg) and 1,1′-bis(diphenylphosphino)ferrocene (584 mg), followed by stirring at 80° C. for 8 hours. After the reaction solution was brought back to room temperature, a 10% aqueous citric acid solution and dichloromethane were added, and the solution was separated. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford benzyl 2′-hydroxy-3-methylbiphenyl-4-carboxylate (6.01 g).

Workup

  1. customwas brought back to room temperature
  2. customthe solution was separated
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8582dccc95214400a26a34acede9123d
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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