Trisodium phosphate dodecahydrate → 4'-n-Propyl-3,5-difluoro-biphenyl-4-ylamine

HRID 413620

반응식

HRID 413620 반응식
O.O.O.O.O.O.O.O.O.O.O.O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].Br[C:22]1[CH:28]=[C:27]([F:29])[C:25]([NH2:26])=[C:24]([F:30])[CH:23]=1.[CH2:31]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)[CH2:32][CH3:33]>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:31]([C:34]1[CH:39]=[CH:38][C:37]([C:22]2[CH:28]=[C:27]([F:29])[C:25]([NH2:26])=[C:24]([F:30])[CH:23]=2)=[CH:36][CH:35]=1)[CH2:32][CH3:33]

참가 물질

6

반응물 3

HCID 61473Trisodium phosphate dodecahydrateHCID 6101914-Bromo-2,6-difluoroanilineHCID 4100861(4-Propylphenyl)boronic acid

생성물 1

HCID 700099564'-n-Propyl-3,5-difluoro-biphenyl-4-ylamine수율 99.5%

시약·촉매·용매 2

HCID 10122028Bis(triphenylphosphine)palladium촉매HCID 962Water용매

실험 절차

348 g trisodiumphosphate dodecahydrate (Merck KGaA, Art. No.106 578) were dissolved in 500 ml of distilled water. Then 8.563 g bis(triphenylphosphine) palladium (Merck KGaA, Art. No. 804 174) and 0.611 g hydaziniumhydroxide (Merck KGaA, Art. No. 804 604) were added. The suspension was stirred for 5 minutes. Then, 126.886 g 4-bromo-2,6-difluoro-aniline, prepared in house, were added. Next 100 g of the p-n-propylphenyl boronic acid, prepared as described above, dissolved in 600 ml dried tetrahydrafurane (Merck KGaA, Art. No.108 107) was added dropwise. The reaction mixture was heated 6 hours under reflux. The organic layer was separated, dried over Na2SO4 and it's solvent evaporated. The isolated crude product (150 g of 4′-n-propyl-3,5-difluoro-biphenyl-4-ylamine was used for the next step of the reaction without further purificatoin.

후처리

  1. addition804 604) were added
  2. additionwere added
  3. dissolutiondissolved in 600 ml
  4. customdried tetrahydrafurane (Merck KGaA, Art. No.108 107)
  5. additionwas added dropwise
  6. temperatureThe reaction mixture was heated 6 hours
  7. temperatureunder reflux
  8. customThe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. customevaporated

출처 및 근거

ORD 기록
ord-4abd16b979e747879e943d62a7d5e4d7
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569505B2

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