Ethanol → 3-Fluoro-5-(hydroxymethyl)benzonitrile

HRID 1260890노트

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HRID 1260890 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:6](OC)=[O:7])#[N:2].C(O)C.[BH4-].[Li+]>O1CCCC1>[F:13][C:11]1[CH:12]=[C:3]([CH:4]=[C:5]([CH2:6][OH:7])[CH:10]=1)[C:1]#[N:2]

참가 물질

5

반응물 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 26597287Methyl 3-cyano-5-fluorobenzoate

생성물 1

HCID 686622523-Fluoro-5-(hydroxymethyl)benzonitrile수율 62.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
55 °C

실험 절차

(Step 2) To a mixed solution of methyl 3-cyano-5-fluorobenzoate (0.55 g) obtained in Step 1 in tetrahydrofuran:ethanol=10:1 (22 ml) was added lithium tetrahydroborate (0.10 g) at 0° C. After stirring at 55° C. for 1 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 3-fluoro-5-(hydroxymethyl)benzonitrile (0.29 g).

후처리

  1. customthe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8bfef8f7a0554b469c0a79b4e87b200c
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470859B2

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