Sodium Carbonate → 2-Phenylfuran

HRID 234380

Reaction equation

HRID 234380 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-79ab1e15d4864314a3d50bf40a967bfc
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Linked notes

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