1,1'-Carbonyldiimidazole → 2-Fluoro-5-(hydroxymethyl)benzonitrile

HRID 2171351노트

반응식

HRID 2171351 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6](O)=[O:7])#[N:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+]>O1CCCC1>[F:12][C:11]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[C:1]#[N:2]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27739323-Cyano-4-fluorobenzoic acidHCID 4311764Sodium borohydride

생성물 1

HCID 27739342-Fluoro-5-(hydroxymethyl)benzonitrile수율 38.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-cyano-4-fluorobenzoic acid (1.00 g, 6.06 mmol) in tetrahydrofuran (THF) (20 mL) was added dropwise CDI (1.47 g, 9.08 mmol) at 0° C. After at room temperature for 30 min, sodium borohydride (0.687 g, 18.2 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic part was separated, dried over Na2SO4, filtered and concentrated. Purification via flash column (petroleum ether/ethyl acetate=10/1) afforded the title product (350 mg).

후처리

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. customThe organic part was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash column (petroleum ether/ethyl acetate=10/1)

출처 및 근거

ORD 기록
ord-bfd939c5df034e318ddb2bc5a3360afa
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051325B2

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