Ethyl 4-chloroacetoacetate → HCID 18757590, compound

HRID 355413Notes

Reaction equation

HRID 355413 reaction equation
[F:1][C:2]1[C:8]([OH:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[OH:4].[Cl:11][CH2:12][C:13](=O)[CH2:14][C:15](OCC)=[O:16]>CS(O)(=O)=O.O>[Cl:11][CH2:12][C:13]1[C:5]2[C:3](=[C:2]([F:1])[C:8]([OH:9])=[C:7]([F:10])[CH:6]=2)[O:4][C:15](=[O:16])[CH:14]=1

Participants

5

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 108445152,4-Difluororesorcinol2×

Product 1

HCID 18757590HCID 18757590, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 2,4-difluororesorcinol (Compound 4, 0.20 g, 1.37 mmol) and ethyl 4-chloroacetoacetate (0.29 g, 1.75 mmol) in 2 mL methanesulfonic acid is kept at room temperature for 2.5 hours, then diluted with 25 mL water. The resulting precipitate is collected on a Buchner funnel and dried to give 134 mg of dimly fluorescent Compound 28 as a colorless powder. This product is purified further by chromatography (silica gel, ethyl acetate/hexanes): Rf =0.45 (EtOAc/hexanes 3:2); 1H NMR (CDCl3 -CD3OD) δ 7.13 (dd, 1H), 6.41 (s, 1H), 4.52 (s, 2H); 19F NMR (CDCl3 -CD3OD) Φ 136.38 (t, 1F), 153.26 (d, 1F).

Workup

  1. customThe resulting precipitate is collected on a Buchner funnel
  2. customdried

Sources & evidence

ORD record
ord-70256bdfe42b4f99b8d3829d7814d5f0
Source dataset
uspto-grants-1998_11
Patent number
US05830912

Reaction notes

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