Potassium Carbonate → 99113-85-6

HRID 915674Notes

Reaction equation

HRID 915674 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:7]([C:4]1[O:5][CH:6]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=1)=[O:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 1354168999113-85-6Yield 41.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Prepare a solution of 4-bromo-2-formylfuran (3.7 g, 21.1 mmol) in 1,2-dimethoxyethane (148 mL). Add phenyl boronic acid (5.16 g, 42.3 mmol), K2CO3 (31.6 mL, 63.4 mmol), Pd2(dba)3 (660 mg, 0.63 mmol), and PPh3 (670 mg, 2.5 mmol). Stir the reaction mixture under nitrogen for 10 minutes at room temperature. After 10 minutes, heat the mixture to 80° C. for 3 days. Wash the reaction mixture with brine (30 mL), dry (Na2SO4), filter, and concentrate. Perform flash chromatography on silica gel eluting with 1:1 hex/ethyl acetate to afford the title compound (1.5 g) as a brown liquid. 1H NMR (CDCl3) δ 9.71 (s, 1H), 7.97 (s, 1H), 6.82-7.55 (m, 6H).

Workup

  1. waitAfter 10 minutes
  2. temperatureheat the mixture to 80° C. for 3 days
  3. washWash the reaction mixture with brine (30 mL)
  4. dry with materialdry (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-fd91e85afe054726b3248ee93b17e434
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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