Iodine → 2-Iodo-4-methylaniline

HRID 532202

반응식

HRID 532202 반응식
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[I:14]I.OS([O-])=O.[Na+]>C(Cl)Cl.O>[I:14][C:4]1[CH:3]=[C:2]([CH3:1])[CH:8]=[CH:7][C:5]=1[NH2:6]

참가 물질

7

반응물 4

HCID 807IodineHCID 7813p-ToluidineHCID 516892Sodium BicarbonateHCID 23665763Sodium Bisulfite

생성물 1

HCID 27640002-Iodo-4-methylaniline수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-methylaniline (53.5 g, 500 mmol) in DCM (200 mL) was added a solution of NaHCO3 (50.4 g) in water (500 mL), and then I2(127 g) was added. The mixture was stirred at rt overnight. The mixture was treated with aqueous NaHSO3 and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and then concentrated in vacuo to afford the product as brown oil (110 g, yield 95%). 1H NMR (300 MHz, CDCl3): δ 7.48 (dd, J=1.8 & 0.6 Hz, 1H), 6.96 (dd, J=8.1 & 1.8 Hz, 1H), 6.67 (d, J=8.1 Hz, 1H), 3.98 (bs, 2H), 2.22 (s, 3H) ppm.

후처리

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-36546288e7d84413b7c8915bda0764ca
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853186B2

연결된 노트

불러오는 중…