3,4-Dichloroaniline → 3-(3,4-Dichloro-phenylamino)-propionic Acid tert-butyl ester

HRID 1096194Notes

Reaction equation

HRID 1096194 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C(C)=CC=CC=1C.Br[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C1(C)C=CC=CC=1>[C:24]([O:23][C:21](=[O:22])[CH2:20][CH2:19][NH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 79372,6-LutidineHCID 256128tert-Butyl 3-bromopropionate

Product 1

HCID 667832463-(3,4-Dichloro-phenylamino)-propionic Acid tert-butyl esterYield 52.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 9.61 g (59.33 mmol) of 3,4-dichloro-phenylamine and 10.21 ml (59.33 mmol) of 2,6-lutidine in 55 ml of toluene was treated slowly with 6.50 ml (59.33 mmol) of tert-butyl 3-bromopropionate and stirred 30 h at reflux temperature. The reaction was then partitioned between 10% aq. KHSO4 solution and EtOAc (3×). The organic phases were washed with 10% aq. NaCl solution, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane:EtOAc 9:1) to yield 8.98 g (52%) of the title compound as off-white solid. MS: 290.0 (MH+, 2Cl).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction was then partitioned between 10% aq. KHSO4 solution and EtOAc (3×)
  3. washThe organic phases were washed with 10% aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (n-heptane:EtOAc 9:1)

Sources & evidence

ORD record
ord-78427fa065704552a9c129bf93f51fd4
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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