Triphenylphosphine → 3-(Bromomethyl)-5-chlorobenzamide

HRID 1260867노트

반응식

HRID 1260867 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([CH2:32]O)[CH:31]=1)[C:26]([NH2:28])=[O:27]>C(#N)C>[Br:20][CH2:32][C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([Cl:22])[CH:31]=1)[C:26]([NH2:28])=[O:27]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 589629763-Chloro-5-(hydroxymethyl)benzamide

생성물 1

HCID 686616453-(Bromomethyl)-5-chlorobenzamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(Step 2) Triphenylphosphine (1.27 g) was suspended in acetonitrile (50 ml), bromine (0.25 ml) was added, and the suspension was stirred for 30 min. 3-Chloro-5-(hydroxymethyl)benzamide (0.90 g) obtained in Step 1 was added to the reaction mixture, and the mixture was stirred at 85° C. for 2 hr. The reaction solution was quenched with water and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1) to give 3-(bromomethyl)-5-chlorobenzamide (0.54 g).

후처리

  1. stirringthe mixture was stirred at 85° C. for 2 hr
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium hydrogen carbonate solution
  5. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1)

출처 및 근거

ORD 기록
ord-ab3beec7dcf5469a9993f80f73a39ff2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470859B2

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