Ethyl bromoacetate → HCID 68554761, compound

HRID 1967583Notes

Reaction equation

HRID 1967583 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][NH:18][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[C:6]([Cl:17])[CH:5]=1)[CH3:25]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 68557310HCID 68557310, compound

Product 1

HCID 68554761HCID 68554761, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Dichloro-4-(4-methoxy-phenoxy)-phenylamine (10.2 g, 0.03 mol), ethyl bromoacetate (5.39 g, 0.03 mol) and diisopropylethylamine (5.1 g, 0.03 mol) in 50 mL of DMF were stirred at 120° C. for 18 h. The reaction mixture was poured in to ice-water. The product was taken up in ethyl acetate, washed with water, brine, dried over sodium sulphate, filtered and concentrated to give the crude product, which was purified by column chromatography over flash silica gel, (hexane:ethyl acetate 90:10) to afford pure [3,5-Dichloro-4-(4-methoxy-phenoxy)-phenylamino]-acetic acid ethyl ester.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography over flash silica gel, (hexane:ethyl acetate 90:10)

Sources & evidence

ORD record
ord-7a1f7391e81b408cbd14a82defb7b7aa
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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