Dimethylformamide → HCID 58483266, compound

HRID 59336Notes

Reaction equation

HRID 59336 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 58483266HCID 58483266, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4336002c571f4c5ba013cf5fcdb4679f
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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