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

HRID 2171351ノート

反応式

HRID 2171351 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 27739342-Fluoro-5-(hydroxymethyl)benzonitrile収率 38.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bfd939c5df034e318ddb2bc5a3360afa
出典データセット
uspto-grants-2015_06
特許番号
US09051325B2

反応ノート

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