Bromine → Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

HRID 266753Notes

Reaction equation

HRID 266753 reaction equation
[Br:1]Br.[CH3:3][CH:4]([CH3:19])[C:5]([C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)=[O:6]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:4]([CH3:19])([CH3:3])[C:5]([C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 12797090Methyl 2-(4-isobutyrylphenoxy)acetate

Product 1

HCID 18918473Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Bromine (2.09 ml) has added dropwise over ten minutes to a stirred solution of the product of step (i) above (9.44 g) in carbon tetrachloride (2001 ml). The solution was stirred for 16 hours, then the solvent was evaporated invacuo to give an orange oil. A solution of this oil, in a small volume of dichloromethane, was filtered through silica and the clear filtrate, on evaporation, gave methyl 4-(2-bromo-2,2-dimethylacetyl)phenoxyacetate, 11.3 g, as a white crystalline solid: m.p. 46°-50° C.; NMR (d6DMSO) δ 8.09 (2H, d), 7.05 (2H, d), 4.92 (2H, s), 3.72 (3H, s), 2.00 (6H, s).

Workup

  1. customthe solvent was evaporated invacuo
  2. customto give an orange oil
  3. filtrationA solution of this oil, in a small volume of dichloromethane, was filtered through silica
  4. customthe clear filtrate, on evaporation

Sources & evidence

ORD record
ord-15233dfd1cdf4cf2a748bde1b1f11366
Source dataset
uspto-grants-1997_07
Patent number
US05652242

Reaction notes

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