Bromine → [4-Bromo-2-(2-bromoacetyl)phenoxy]acetic acid ethyl ester

HRID 910034Notes

Reaction equation

HRID 910034 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14](=[O:16])[CH3:15])[CH3:2].[Br:18]Br>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14](=[O:16])[CH2:15][Br:18])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

Product 1

HCID 57658801[4-Bromo-2-(2-bromoacetyl)phenoxy]acetic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled (0° C.) solution of (2-acetyl-4-bromophenoxy)acetic acid ethyl ester (2.5 g, 8.3 mmol) in CHCl3 (25 mL) was slowly added bromine (425 uL, 8.3 mmol). After completion the reaction mixture was allowed to stir at room temperature for 1 hour. The mixture was partitioned between CH2Cl2 and brine. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (2.97 g, 7.8 mmol, 94%): 1H NMR (CDCl3): δ 1.35 (t, 3H), 4.32 (q, 2H), 4.75 (s, 2H), 4.76 (s, 2H), 6.77 (d, 1H), 7.60 (dd, 1H), 7.97 (s, 1H)

Workup

  1. customThe mixture was partitioned between CH2Cl2 and brine
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-362a6e885afd4e0ab0c31f51c8644df9
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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