Bromine → 2,4-Bis(acetoxymethyl)bromobenzene

HRID 1937747Notes

Reaction equation

HRID 1937747 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH:7]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:22]Br.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][C:11]=1[Br:22])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 24408BromineHCID 24437Sodium SulfiteHCID 517045Sodium AcetateHCID 12571717m-Xylylene glycol diacetate

Product 1

HCID 99482912,4-Bis(acetoxymethyl)bromobenzeneYield 97.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of m-xylylene glycol diacetate (28.4 g) and sodium acetate (55.2 g) dispersed in glacial acetic acid (130 ml) was added dropwise bromine (102.5 g) over 30 min at 15-20 C., and the mixture was stirred at 20-30° C. for 13 hr. The reaction mixture was poured into 10% aqueous sodium sulfite solution (700 ml) in an ice bath. The mixture was stirred and extracted twice with ethyl acetate (250 ml). The ethyl acetate layer was washed 3 times with 10% aqueous sodium hydrogencarbonate solution (300 ml) and the solvent was evaporated to give an about 93:7 mixture (37.6 g, 97.6%) of 2,4-bis(acetoxymethyl)bromobenzene and 2,6-bis(acetoxymethyl)bromobenzene as a yellow oil. 2,4-bis(Acetoxymethyl)bromobenzene was isolated by preparative HPLC and used in the measurement. the mixture:

Workup

  1. stirringThe mixture was stirred
  2. extractionextracted twice with ethyl acetate (250 ml)
  3. washThe ethyl acetate layer was washed 3 times with 10% aqueous sodium hydrogencarbonate solution (300 ml)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8a4bef1db6314cf1a5a6a5b1cb79dcb0
Source dataset
uspto-grants-2002_05
Patent number
US06395910B2

Reaction notes

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