Bromine → 2-Bromo-1-[5-(4-nitro-phenyl)-furan-2-yl]-ethanone

HRID 1730634Notes

Reaction equation

HRID 1730634 reaction equation
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH3:19])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]>C(Cl)(Cl)(Cl)Cl>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH2:19][Br:1])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 44054061-[5-(4-Nitro-phenyl)-furan-2-yl]-ethanone

Product 1

HCID 71723152-Bromo-1-[5-(4-nitro-phenyl)-furan-2-yl]-ethanoneYield 93%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 38 g (0.24 mole) of bromine in 100 ml of CCl4 was added dropwise over 50 min to a stirred, refluxing mixture of 55 g (0.24 mole) of methyl 5-(p-nitrophenyl)-2-furyl ketone and 1200 ml of CCl4. After the addition was complete, the reaction mixture was heated under reflux for 3/4 hr and allowed to stand at room temperature overnight. The yellow solid was collected by filtration to give 69 g (93%) of bromomethyl 5-(p-nitrophenyl)-2-furyl ketone, m.p. 153°-162°.

Workup

  1. temperaturerefluxing
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 3/4 hr
  5. filtrationThe yellow solid was collected by filtration

Sources & evidence

ORD record
ord-8e1db78540e64c1b96bb493a92d9be68
Source dataset
uspto-grants-1976_11
Patent number
US03993657

Reaction notes

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