Bromine → 2,4-Bis(acetoxymethyl)bromobenzene

HRID 585335Notes

Reaction equation

HRID 585335 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.

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-43c05c81f19349d0bd724e52eee4c3c2
Source dataset
uspto-grants-2005_08
Patent number
US06930211B2

Reaction notes

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