O-Toluidine → 4-[1-(Bromo-difluoro-methyl)-1,2,2,2-tetrafluoro-ethyl]-2-methyl-phenylamine

HRID 1824581

반응식

HRID 1824581 반응식
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])O.[Na+].[Br:22][C:23]([F:32])([F:31])[C:24](Br)([F:29])[C:25]([F:28])([F:27])[F:26].C(=O)([O-])[O-].[Na+].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.COC(C)(C)C.O>[CH3:16][C:11]1[CH:12]=[C:13]([C:24]([F:29])([C:25]([F:28])([F:27])[F:26])[C:23]([Br:22])([F:32])[F:31])[CH:14]=[CH:15][C:10]=1[NH2:9]

참가 물질

9

반응물 5

HCID 7242O-ToluidineHCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 695791,2-Dibromo-1,1,2,3,3,3-hexafluoropropaneHCID 516892Sodium Bicarbonate

생성물 1

HCID 104496444-[1-(Bromo-difluoro-methyl)-1,2,2,2-tetrafluoro-ethyl]-2-methyl-phenylamine

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 15413tert-Butyl methyl ether용매2회

반응 조건

온도
40 °C

실험 절차

First 154.36 g (0.887 mol) of sodium dithionite and then 50 g (0.467 mol) of o-toluidine (2-methylaniline) were added at room temperature to a mixture of 900 ml of water, 350 ml of tert-butyl methyl ether, 74.48 g (0.887 mol) of sodium hydrogencarbonate and 12.68 g of tetra-n-butylammonium hydrogensulphate. Subsequently, a solution of 274.684 g of 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane in 100 ml of tert-butyl methyl ether was added dropwise at 35–40° C. and, on completion of addition, the mixture was stirred at 40° C. for a further 18 h. If necessary, sodium carbonate was used to adjust to a pH of 5 and the organic phase was removed, dried and concentrated. The remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.

후처리

  1. customthe organic phase was removed
  2. customdried
  3. concentrationconcentrated
  4. distillationThe remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.

출처 및 근거

ORD 기록
ord-d062f89ffb4a489990a2eedd0881b43c
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041852B2

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