Dimethylformamide → 3-Phenylbenzaldehyde

HRID 78046

반응식

HRID 78046 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[O:14]1CCC[CH2:15]1.C([Li])CCC.CN(C)C=O>O>[C:8]1([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH:15]=[O:14])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 164493-BromobiphenylHCID 178418339Butyllithium

생성물 1

HCID 1210533-Phenylbenzaldehyde수율 79%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

To a mixture of 3-bromobiphenyl (0.50 mL, 3.0 mmol) and tetrahydrofuran (8 mL) was added n-butyl lithium (2.6 mL, 1.5 M n-hexane solution, 3.9 mmol) under nitrogen atmosphere at −78° C., which was stirred for 20 minutes at that temperature. N,N-dimethylformamide (0.35 mL, 4.5 mmol) was added to the reaction mixture at the same temperature, and the temperature was gradually raised to 0° C. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (430 mg, 79%).

후처리

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. concentrationwas concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-f788669398444106b6c221dc78b9d8a6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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