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

HRID 59336ノート

反応式

HRID 59336 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 58483266Ethyl 6-chloro-2-fluoro-3-formylbenzoate収率 35.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4336002c571f4c5ba013cf5fcdb4679f
出典データセット
uspto-grants-2016_09
特許番号
US09439890B2

反応ノート

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