Aniline → 9,9-Dimethyl-N-phenyl-9H-fluoren-2-amine

HRID 2275914노트

반응식

HRID 2275914 반응식
Br[C:2]1[C:14]2[C:13]([CH3:16])([CH3:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:13]1([CH3:16])[C:12]2[CH:11]=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:9]=[CH:8][C:7]=2[C:6]2[C:14]1=[CH:2][CH:3]=[CH:4][CH:5]=2

참가 물질

7

반응물 3

HCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 667979641-bromo-9,9-dimethyl-9H-fluorene

생성물 1

HCID 187301779,9-Dimethyl-N-phenyl-9H-fluoren-2-amine

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 1140Toluene용매

실험 절차

50 g of bromo-9,9-dimethyl-9H-fluorene (183 mmol), 20 ml of aniline (220 mmol), 1.5 g of DPPF (2.7 mmol), 0.5 g of palladium(II)acetate and 45 g of sodium tert-butoxide (486 mmol) are heated at the boil in 1.5 l of toluene under a protective atmosphere for 18 h. The mixture is subsequently partitioned between toluene and water, and the organic phase is washed three times with water and dried over Na2SO4 and evaporated in a rotary evaporator. The residue which remains is recrystallised from heptane/ethyl acetate. The yield is 31.2 g (110 mmol, 52%).

후처리

  1. customThe mixture is subsequently partitioned between toluene and water
  2. washthe organic phase is washed three times with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in a rotary evaporator
  5. customThe residue which remains is recrystallised from heptane/ethyl acetate

출처 및 근거

ORD 기록
ord-51723603cf6f4febaa1c485f18ed745b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126970B2

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