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

HRID 597283Notes

Reaction equation

HRID 597283 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>[Br:1][C:2]1[C:3]2[O:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 1

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

Product 1

HCID 30163557-Bromo-3-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Polyphosphoric acid (4200 g.) and alpha-(2-bromophenoxy)acetophenone from Example 1 (596 g., 2.05 mole) are heated and stirred well at about 120° to 125° C. internal temperature for four hours. The reaction mixture is then poured into stirred ice and water (about 8 l. total volume) to give a suspension of white solid. The solid is collected and washed with water, cold dilute sodium hydroxide solution and water until the wash is neutral. The solid is recrystallized from hexane to give white crystals of 7-bromo-3-phenylbenzofuran, m.p. 72°-74° C.

Workup

  1. additionThe reaction mixture is then poured
  2. customto give
  3. additiona suspension of white solid
  4. customThe solid is collected
  5. washwashed with water, cold dilute sodium hydroxide solution and water until the wash
  6. customThe solid is recrystallized from hexane

Sources & evidence

ORD record
ord-c86e454fa2884b7c9d1c30d8f1da4ab2
Source dataset
uspto-grants-1977_03
Patent number
US04013692

Reaction notes

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