Allyl Alcohol → 3-(4-Nitro-2-(trifluoromethyl)phenyl)propionaldehyde

HRID 1912878노트

반응식

HRID 1912878 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([OH:18])[CH:16]=[CH2:17].C(N(CC)CC)C>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:17][CH2:16][CH:15]=[O:18])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

참가 물질

7

반응물 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 1361982-Bromo-5-nitrobenzotrifluoride

생성물 1

HCID 231552963-(4-Nitro-2-(trifluoromethyl)phenyl)propionaldehyde수율 166.1%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

In 3 mL of dimethylformamide, 50 mg (0.19 mmol) of 4-bromo-3-(trifluoromethyl)nitrobenzene was dissolved, and 33 mg (0.56 mmol) of allyl alcohol, 43 mg (0.19 mmol) of tetrabutylammonium bromide, 2.1 mg (5 mol %) of palladium acetate and 52 μL (0.37 mmol) of triethylamine were added thereto and the mixture solution was stirred in an argon atmosphere at 90° C. for two hours. The reaction solution was partitioned between water and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The product was purified by a silica gel column (n-hexane:ethyl acetate=5:1) to obtain 78 mg (79%) of a target product as a pale yellow oil.

후처리

  1. customThe reaction solution was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with a saturated sodium chloride solution
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by a silica gel column (n-hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-3c38739d11ca4ac19714f837354af43e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609656B2

반응 노트

불러오는 중…