Trifluoroacetic acid → 5-Chloro-3-iodo-2-methylaniline

HRID 2367138

반응식

HRID 2367138 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([I:17])[C:5]([CH3:16])=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([I:17])[C:5]([CH3:16])=[C:6]([CH:7]=1)[NH2:8]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86617520HCID 86617520, 화합물

생성물 1

HCID 247292075-Chloro-3-iodo-2-methylaniline수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,1-dimethylethyl (5-chloro-3-iodo-2-methylphenyl)carbamate (5 g, 13.6 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid (10 mL). The solution was stirred at ambient temperature for 2 hours, then concentrated in-vacuo. The resultant residue was partitioned between saturated sodium bicarbonate and ethyl acetate. The aqueous portion was extracted twice with ethyl acetate. The combined organic portions were washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford an orange residue which was purified by column chromatography (silica gel, 5% ethyl acetate in hexane). The product was isolated to afford 3.05 g, 11.4 mmol (84%) of 5-chloro-3-iodo-2-methylaniline as a yellow solid. 1H NMR (400 MHz, CDCl3): 7.26 (d, 1H), 6.64 (d, 1H), 3.78 (br s, 2H), 2.28 (s, 3H); MS (EI) for C7H7Cl1N: 268 (MH+).

후처리

  1. concentrationconcentrated in-vacuo
  2. customThe resultant residue was partitioned between saturated sodium bicarbonate and ethyl acetate
  3. extractionThe aqueous portion was extracted twice with ethyl acetate
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo
  8. customto afford an orange residue which
  9. customwas purified by column chromatography (silica gel, 5% ethyl acetate in hexane)
  10. customThe product was isolated

출처 및 근거

ORD 기록
ord-8e9dac0c98d840399d69a8542c6a9630
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697737B2

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