Water → HCID 118162005, compound

HRID 1482867Notes

Reaction equation

HRID 1482867 reaction equation
Br[C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:12][C:5]1[CH:4]=[CH:3][C:2]([C:19]2[CH:18]=[CH:17][C:16]([O:15][C:14]([F:13])([F:25])[F:26])=[CH:21][CH:20]=2)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77683Methyl 5-bromosalicylateHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 118162005HCID 118162005, compoundYield 84.7%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 5-bromosalicylate (5 g, 21.6 mmol), 4-(trifluoromethoxy)phenylboronic acid (4.43 g, 21.6 mmol), potassium carbonate (10 g) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (800 mg, 1.09 mmol) were combined in 10 mL DMF. 5 mL water was added and the mixture was stirred at 50° C. for 60 minutes. The reaction mixture was diluted with 300 mL ethyl acetate, washed with water and brine and evaporated under vacuum. Flash chromatographic purification on 120 g silica gel with 0-100% ethyl acetate in hexane gave methyl 4-hydroxy-4′-(trifluoromethoxy)-[1,1′-biphenyl]-3-carboxylate (5.7 g, 18.3 mmol).

Workup

  1. washwashed with water and brine
  2. customevaporated under vacuum
  3. customFlash chromatographic purification on 120 g silica gel with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8310f27afae94bbfa1c648e9e0dc85d6
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

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