N-bromobutanimide → 5-Bromomethyl-2,7-dibromo-3-phenylbenzofuran

HRID 262091

Reaction equation

HRID 262091 reaction equation
[Br:1][C:2]1[O:3][C:4]2[C:16]([Br:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:18][C:14]1[CH:15]=[C:16]([Br:17])[C:4]2[O:3][C:2]([Br:1])=[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]=2[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 213199312,7-Dibromo-5-methyl-3-phenylbenzofuran

Product 1

HCID 213199325-Bromomethyl-2,7-dibromo-3-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture containing 68.7 g. (0.19 mole) of 2,7-dibromo-5-methyl-3-phenylbenzofuran and 35.5 g. (0.19 mole) of N-bromosuccinimide in one liter of carbon tetrachloride is irradiated with a bulb simulating sunlight for two hours. An additional 10 g. of N-bromosuccinimide is added, and irradiation is continued for one hour. The mixture is cooled and filtered. The filtrate is evaporated to a brown oil which crystallizes when triturated with hexane to provide solid 5-bromomethyl-2,7-dibromo-3-phenylbenzofuran.

Workup

  1. additionA mixture containing 68.7 g
  2. customirradiation
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. customThe filtrate is evaporated to a brown oil which
  6. customcrystallizes when
  7. customtriturated with hexane

Sources & evidence

ORD record
ord-5f454f9e2cd6478b827e3ec51942ce11
Source dataset
uspto-grants-1979_05
Patent number
US04153619

Linked notes

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