Sodium Carbonate → 2-Phenylfuran

HRID 1899736Notes

Reaction equation

HRID 1899736 reaction equation
Br[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:13]1(OB(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC>[C:13]1([C:2]2[O:3][CH:4]=[CH:5][CH:6]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 2776190Furan, 2-bromo-

Product 1

HCID 5193632-Phenylfuran

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8058HexaneSolvent

Procedure

2-phenylfuran was prepared by the method of Example 32C from 2-bromofuran (0.93 g, 6.3 mmol), sodium carbonate (18 ml of 2M aqueous solution), phenyl boric acid (0.93 g, 7.6 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.36 g, 0.32 mmol). Flash chromatography with hexane provided 0.79 g (87% yield) of a colorless liquid.

Sources & evidence

ORD record
ord-ec8007dc19d04b77bd186faa39a747c6
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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