Sodium Bicarbonate → HCID 67218105, compound

HRID 1505276Notes

Reaction equation

HRID 1505276 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([C:19](F)(F)F)=[CH2:18])[CH:14]=[C:13]([Cl:23])[CH:12]=1.C(=O)([O-])O.[Na+]>C(OC(=O)C)C>[CH2:2]([O:3][C:4]([C:6]1[CH2:18][C:17]([C:15]2[CH:14]=[C:13]([Cl:23])[CH:12]=[C:11]([Cl:10])[CH:16]=2)([CH3:19])[O:8][N:7]=1)=[O:5])[CH3:1]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 67218105HCID 67218105, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

A solution of ethyl chlorooximidoacetate (9.0 g, 59.1 mmol) in ethylacetate (30 ml) was added at ambient temperature with a syringe pump over a period of 40 h to a suspension of 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (prepared according to WO 2005/085216) (9.5 g, 39.4 mmol) and sodium hydrogen carbonate (15.9 g, 189 mmol) in ethylacetate (85 ml). The reaction mixture was diluted with ethylacetate and washed with water. The organic phase was separated dried over sodium sulfate and concentrated. The residue was purified by chromatography over silica (cyclohexane/ethylacetate; 4/1) to give 8.9 of a yellow oil. 1H-NMR (CDCl3, 400 MHz): 7.45 (m, 3H), 4.49 (q, 2H), 3.96 (d, 1H), 3.59 (d, 1H), 1.40 (t, 3H).

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography over silica (cyclohexane/ethylacetate; 4/1)
  6. customto give 8.9 of a yellow oil

Sources & evidence

ORD record
ord-1d2c51640a464206b82af29dfe073899
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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