Acetic Acid → Methyl 2-(4-amino-3-bromophenyl)acetate

HRID 350446노트

반응식

HRID 350446 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O[Na])(C)=O.O.O.O.CC(O)=O>CO.O>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:3][C:2]=1[Br:1]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 23512304Methyl (3-bromo-4-nitrophenyl)acetateHCID 178476686sodium;acetate;trihydrate

생성물 1

HCID 15462911Methyl 2-(4-amino-3-bromophenyl)acetate수율 69%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
90 °C

실험 절차

A mixture of methyl 3-bromo-4-nitrophenylacetate (14.8 g, 53.8 mmol), reduced iron powder (9.62 g, 172 mmol), AcONa.3H2O (7.32 g, 53.8 mmol) and AcOH (20.0 ml) in MeOH/H2O (150/600 ml) was heated at 90° C. for 1 h. After cooled to room temperature, the reaction mixture was filtered through Celite and the filtered cake was washed with MeOH. The combined filtrate were evaporated and extracted with EtOAc. The extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel [400 g, CHCl3/EtOAc (20/1)] to give methyl 4-amino-3-bromophenylacetate (9.01 g, 69%) as a brown oil. 1H-NMR (CDCl3) δ 3.48 (s, 2H), 3.68 (s, 3H), 4.05 (br, 2H), 6.69 (d, J=8.3 Hz, 1H), 7.00 (dd, J=8.1, 2.0 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H).

후처리

  1. temperatureAfter cooled to room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. washthe filtered cake was washed with MeOH
  4. customThe combined filtrate were evaporated
  5. extractionextracted with EtOAc
  6. washThe extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel [400 g, CHCl3/EtOAc (20/1)]

출처 및 근거

ORD 기록
ord-34b91b524ede4458baa24574c7e61c92
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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