(5-bromo-1-benzofuran-2-yl)(phenyl)methanone → 2-Benzyl-5-bromo-1-benzofuran

HRID 2075165Notes

Reaction equation

HRID 2075165 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=O)=[CH:7][C:6]=2[CH:18]=1.C([BH3-])#N.[Na+]>[I-].[Zn+2].[I-].ClCCCl>[CH2:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:18][C:6]=2[CH:7]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 801609(5-bromo-1-benzofuran-2-yl)(phenyl)methanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 227689092-Benzyl-5-bromo-1-benzofuran

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

(5-bromobenzofuran-2-yl)(phenyl)methanone (2.0 g, 6.6 mmol), sodium cyanoborohydride (3.2 g, 51 mmol), zinc iodide (2.6 g, 13.2 mmol) and 1,2-dichloroethane (50 mL) were combined and heated to reflux for overnight. The mixture was cooled, quenched with saturated ammonium chloride, acidified with concentrated HCl and stirred for 30 minutes. The layers were separated, the aqueous layer was extracted with dichloromethane (2×100 mL) and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (ISCO system, 20% dichloromethane in hexanes) to give the product as a white solid: 1H NMR (400 MHz, CDCl3) δ7.59 (s, 1H), 7.27-7.34 (m, 7H), 6.32 (s, 1H), 4.10 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for overnight
  3. temperatureThe mixture was cooled
  4. customquenched with saturated ammonium chloride
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
  7. washthe combined organic layers were washed with water (50 mL) and brine (50 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (ISCO system, 20% dichloromethane in hexanes)

Sources & evidence

ORD record
ord-af3dabb7d4d444478055e3a44cae6c3a
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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