Dimethylformamide → Ethyl 6-chloro-2-fluoro-3-formylbenzoate

HRID 508829노트

반응식

HRID 508829 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Li+].CC([N-]C(C)C)C.CN([CH:25]=[O:26])C>C1COCC1>[Cl:1][C:2]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([F:13])[C:10]([CH:25]=[O:26])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 43389523Ethyl 2-chloro-6-fluorobenzoate

생성물 1

HCID 58483266Ethyl 6-chloro-2-fluoro-3-formylbenzoate수율 35.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cold solution of ethyl 2-chloro-6-fluorobenzoate (0.500 g, 24.7 mmol) in THF (35 mL) was added LDA (6.6 g, 61.8 mmol) at −78° C. The reaction mixture was stirred for 2 h at same temperature, followed by addition of DMF (2.7 g, 37 mmol). The reaction mixture was further stirred for 2 h at same temperature. The reaction mass was quenched in dilute HCl, extracted with ethyl acetate and concentrated to afford crude product which was further purified by column chromatography eluting with EtOAC: pet.ether to afford 2.00 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 1.31 (t, 3H), 4.42 (q, 2H), 7.94-7.99 (m, 2H), 10.14 (s, 1H).

후처리

  1. stirringThe reaction mixture was further stirred for 2 h at same temperature
  2. customThe reaction mass was quenched in dilute HCl
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas further purified by column chromatography
  7. washeluting with EtOAC

출처 및 근거

ORD 기록
ord-393455fea6ab456090b792ed5065c735
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

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