Bromine → 5-(2-Bromoacetyl)-1,3-phenylene diacetate

HRID 1421946Notes

Reaction equation

HRID 1421946 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:10]=1)(=[O:3])[CH3:2].[Br:18]Br>C(=S)=S>[C:12]([O:11][C:9]1[CH:8]=[C:7]([C:15](=[O:17])[CH2:16][Br:18])[CH:6]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:10]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 6880155-Acetyl-1,3-phenylene diacetate

Product 1

HCID 187073195-(2-Bromoacetyl)-1,3-phenylene diacetate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Conditions

Temperature
50 °C

Procedure

4 g of 3',5'-diacetyloxyacetophenone was suspended in 75 ml of carbon disulfide. Thereto was dropwise added a solution of 0.90 ml of bromine dissolved in 25 ml of carbon disulfide, at room temperature in about 1 hour. The system was heated to about 50° C. occasionally in the course of dropwise addition and, each time when a reaction started, the system was returned to room temperature and stirred. After the completion of the dropwise addition, stirring was conducted at room temperature for 1 hour. After the completion of the reaction, the solvent was removed by distillation to obtain 5.53 g of 3',5'-diacetyloxy-2-bromoacetophenone as brown crystals.

Workup

  1. customwas returned to room temperature
  2. additionAfter the completion of the dropwise addition
  3. stirringstirring
  4. customAfter the completion of the reaction
  5. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-55f32c5ca21a442db67e5bf31cd2baa4
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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