Toluene → 2-Phenylfuran

HRID 659105

Reaction equation

HRID 659105 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(C)C=CC=CC=1>CCO>[C:10]1([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7961BromobenzeneHCID 10796Cesium carbonateHCID 2734357Furan-2-boronic acid

Product 1

HCID 5193632-Phenylfuran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

Furan-2-boronic acid (22) (3.6 g, 32.14 mmol) was coupled to bromobenzene (21) (4.2 g, 26.79 mmol) using Method E, except that Cs2CO3 (17.47 g, 53.58 mmol), Pd(PPha)4 (6.20 g, 0.54 mmol), toluene (25 mL) and EtOH (25 mL) were used and the reaction heated in a CEM Discover microwave at 140° C. (200 W, 200 psi). The crude product was purified by dry-flash chromatography eluting with EtOAc in heptane to yield the title compound. Yield: 2.94 g, 62%; LC tr 1.50 min; HPLC Purity: 84%

Workup

  1. customThe crude product was purified by dry-flash chromatography
  2. washeluting with EtOAc in heptane

Sources & evidence

ORD record
ord-c5527ea8e52d4a509b9aae5f8e6b5360
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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