Benzenamine, 3-bromo-4-methyl- → 5-Bromo-2-iodo-4-methylaniline

HRID 523244

반응식

HRID 523244 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[I:10]N1C(=O)CCC1=O.[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+]>C(Cl)Cl>[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:6]([I:10])=[C:4]([CH:3]=1)[NH2:5]

참가 물질

5

반응물 3

HCID 82187Benzenamine, 3-bromo-4-methyl-HCID 120273N-IodosuccinimideHCID 10883201Bis(pyridine)iodonium tetrafluoroborate

생성물 1

HCID 1177764315-Bromo-2-iodo-4-methylaniline수율 83.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3-bromo-4-methylaniline (5.00 g, 26.9 mmol), N-iodosuccinimide (4.53 g, 20.2 mmol) and bis(pyridine)iodonium tetrafluoroborate (2.70 g, 7.26 mmol) in DCM (100 mL) was stirred at room temperature overnight. The mixture was diluted with DCM, washed sequentially with saturated aqueous NaHSO3 and water, and dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (sequentially 1%, 2% and 3%), to provide 5-bromo-2-iodo-4-methylaniline as a yellow solid (5.27 g, 63% yield). Mass spectrum m/z 312, 314 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 7.49 (d, J=0.6 Hz, 1H), 6.94 (s, 1H), 4.17-3.91 (br.s, 2H), and 2.25 (s, 3H).

후처리

  1. washwashed sequentially with saturated aqueous NaHSO3 and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with EtOAc-hexanes (sequentially 1%, 2% and 3%),

출처 및 근거

ORD 기록
ord-6b1c575cf99143dd801aea8b8ea68062
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334290B2

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