3-Bromo-5-fluorobenzaldehyde → 3-Butyl-5-fluorobenzaldehyde

HRID 20454

반응식

HRID 20454 반응식
[Br-].[CH2:2]([Zn+])[CH2:3][CH2:4][CH3:5].Br[C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([F:16])[CH:15]=1)[CH:11]=[O:12]>O1CCCC1>[CH2:2]([C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([F:16])[CH:15]=1)[CH:11]=[O:12])[CH2:3][CH2:4][CH3:5]

참가 물질

4

반응물 2

HCID 219862463-Bromo-5-fluorobenzaldehydeHCID 178448256HCID 178448256, 화합물

생성물 1

HCID 862366793-Butyl-5-fluorobenzaldehyde수율 77.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add butylzinc bromide (49.3 mL, 24.6 mmol, 0.5 M in THF) followed by Pd(dppf)2Cl2 dichloromethane complex (1.01 g, 1.23 mmol) to a solution of 3-bromo-5-fluorobenzaldehyde (5.00 g, 24.6 mmol) in tetrahydrofuran (123.1 mL). Stir at room temperature in a sealed vessel flushed with nitrogen for 18 hours. Add saturated aqueous ammonium chloride (125 mL). Separate the layers and extract the aqueous layer with ethyl acetate (1×300 mL). Wash combined organic layers with saturated aqueous sodium chloride, dry over magnesium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with 0-10% ethyl acetate in hexanes to provide the title compound (3.43 g, 77.3%).

후처리

  1. customflushed with nitrogen for 18 hours
  2. customSeparate the layers
  3. extractionextract the aqueous layer with ethyl acetate (1×300 mL)
  4. washWash
  5. dry with materialdry over magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. washSubject residue to silica gel chromatography, eluting with 0-10% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-247fdbf2390840ff8faa78031ab71724
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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