Potassium Phosphate, Tribasic → HCID 67145378, compound

HRID 2273704Notes

Reaction equation

HRID 2273704 reaction equation
Br[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13](/B(O)O)=[CH:14]\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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>[F:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 5702628Styrylboronic acidHCID 7210837Methyl 2-bromo-4-fluorobenzoate

Product 1

HCID 67145378HCID 67145378, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-bromo-4-fluorobenzoate (1.00 g), (E)-styrylboronic acid (0.89 g), tetrakis(triphenylphosphine)palladium(0) (0.50 g), and K3PO4 (2.28 g) were stirred in dioxane (17 mL) at 90° C. for 24 hours. The reaction mixture chromatographed on silica gel with 1-5% ethyl acetate/hexanes. The product in methanol (10 ml) was added to 20 wt % of fresh dry 5% Pd—C and stirred 4 days with H2 in a pressure bottle. The mixture was filtered through a nylon membrane and concentrated.

Workup

  1. customThe reaction mixture chromatographed on silica gel with 1-5% ethyl acetate/hexanes
  2. additionThe product in methanol (10 ml) was added to 20 wt %
  3. dry with materialof fresh dry 5% Pd—C
  4. filtrationThe mixture was filtered through a nylon membrane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6bbf687a232e4d83a3e8529f35ddf51a
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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