Triethylamine → 2-(2,3,6-Trifluoro-benzylidene)-malonic Acid Dimethyl Ester

HRID 564304Notes

Reaction equation

HRID 564304 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH:9](O)[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=1[F:18])[C:5]([O:7][CH3:8])=[O:6].CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[C:4](=[CH:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=1[F:18])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 589506072-[Hydroxy-(2,3,6-trifluoro-phenyl)-methyl]-malonic Acid Dimethyl Ester

Product 1

HCID 584453022-(2,3,6-Trifluoro-benzylidene)-malonic Acid Dimethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[Hydroxy-(2,3,6-trifluoro-phenyl)-methyl]-malonic acid dimethyl ester (13 g, 44.5 mmol) and NEt3 (99, 89 mmol) were dissolved in 300 mL CH2Cl2. MsCl (10.3 g, 89 mmol) was then added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture washed with 1N HCl solution (200 mL×2), brine (100 mL), dried over Na2SO4 and concentrated. The product was purified by column chromatography using EtOAc/Hexane as eluent (gradient from 0/100 to 25/75 in 40 min, 6.5 g, 53%). 1H NMR (CDCl3 400 MHz) δ 7.71 (s, 1H), 7.20 (m, 1H), 6.89 (m, 1H), 3.87 (s, 3H), 3.80 (s, 3H).

Workup

  1. washThe reaction mixture washed with 1N HCl solution (200 mL×2), brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography
  5. custom(gradient from 0/100 to 25/75 in 40 min, 6.5 g, 53%)

Sources & evidence

ORD record
ord-6375ebd5437c40f5b95607b13c181a5e
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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