Ethyl bromoacetate → HCID 68557314, compound

HRID 1967575Notes

Reaction equation

HRID 1967575 reaction equation
[CH:1]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=1[Cl:17])([CH2:3][CH3:4])[CH3:2].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][NH:16][C:12]1[CH:11]=[C:10]([Cl:17])[C:9]([O:8][C:7]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH:6]=2)=[C:14]([Cl:15])[CH:13]=1)[CH3:29]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 68554795HCID 68554795, compound

Product 1

HCID 68557314HCID 68557314, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To 4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenylamine (71.8 g, 0.21 mol) was added ethyl bromoacetate (35.26 g, 0.21 mol) and diisopropylethyl amine (27.92 g, 0.21 mol) in DMF (718 mL) 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 H2O, brine & dried over sodium sulphate, filtered and concentrated to give the crude product. The crude product was purified by column chromatography over flash silica gel (Hexane:Ethylacetate 90:10) to afford the pure product [4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenylamino]-acetic acid ethyl ester. (48.0 g, 54% yield)

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe crude product was purified by column chromatography over flash silica gel (Hexane:Ethylacetate 90:10)

Sources & evidence

ORD record
ord-ed1cbbd71c574aaf9d1e641c44258aae
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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