2-(2-Bromophenoxy)-1-phenylethan-1-one → 7-Bromo-3-phenylbenzofuran

HRID 322028Notes

Reaction equation

HRID 322028 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O>O>[C:8]1([C:6]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:2]([Br:1])[C:3]=3[O:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 30163542-(2-Bromophenoxy)-1-phenylethan-1-one

Product 1

HCID 30163557-Bromo-3-phenylbenzofuranYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-(2-bromophenoxy)-1-phenyl-1-ethanone (6.31 g) and polyphosphoric acid (285 g) was stirred at 95° C. for 6 h. The resulting solution was cooled to 50° C. , poured in water (2 L), extracted with Et2O (2×1 L). The combined organic extracts were washed with water (4×500 ml) and brine, dried over MgSO4 and concentrated. The residual solid was filtered on a plug of silica gel using Et2O. Recrystallization in hot hexane yielded the title compound (4.63g; 78%).

Workup

  1. temperatureThe resulting solution was cooled to 50° C.
  2. extractionextracted with Et2O (2×1 L)
  3. washThe combined organic extracts were washed with water (4×500 ml) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. filtrationThe residual solid was filtered on a plug of silica gel
  7. customRecrystallization in hot hexane

Sources & evidence

ORD record
ord-6cdbed8943fb48f68118e840327e7135
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Reaction notes

Loading…