Chlorosuccinimide → HCID 86707790, compound

HRID 2174363Notes

Reaction equation

HRID 2174363 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:9][C:8]([OH:19])([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[N:17][OH:18])=[CH:12][CH:11]=2)[CH2:7]1)=[O:5])[CH3:2].ClN1C(=O)CCC1=O.C(=O)([O-])O.[K+].[Cl:33][C:34]1[CH:39]=[C:38]([C:40]([C:42]([F:45])([F:44])[F:43])=[CH2:41])[CH:37]=[C:36]([Cl:46])[C:35]=1[Cl:47]>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:9][C:8]([OH:19])([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH2:41][C:40]([C:38]4[CH:37]=[C:36]([Cl:46])[C:35]([Cl:47])=[C:34]([Cl:33])[CH:39]=4)([C:42]([F:45])([F:44])[F:43])[O:18][N:17]=3)=[CH:14][CH:15]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86707789HCID 86707789, compound

Product 1

HCID 86707790HCID 86707790, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-hydroxy-3-[4-(hydroxyimino-methyl)-phenyl]-cyclobutane carboxylic acid ethyl ester (Preparation 2, 4.7 g, 17.87 mmol) in DMF (10 mL) was added N-chloro succinimide (2.61 g, 19.65 mmol) and heated at 50° C. for 1 hour. After complete consumption of starting material, reaction was cooled to 0° C., potassium hydrogen carbonate (2.68 g, 26.88 mmol) was added followed by addition of pre dissolved solution of 1,2,3-trichloro-5-(1-trifluoromethyl-vinyl)-benzene (5.40 g, 19.65 mmol). Resulting reaction mixture was stirred at room temperature for 16 hours. After consumption of chloro intermediate, reaction mixture was diluted with EtOAc (50 mL), washed with water (5×30 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. Purification was done by column chromatography (silica gel, 100-200 mesh). Compound was eluted using 15% ethyl acetate in hexane as eluent to afford white sticky solid (4.7 g, 49%). 1H NMR (400 MHz, CDCl3) δ 1.28 (t, J=9.36 Hz, 3H), 2.57-2.62 (m, 2H), 2.83-2.90 (m, 3H), 3.68 (d, J=17.28 Hz, 1H), 4.08 (d, J=17.16 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 7.55-7.57 (m, 2H), 7.64-7.67 (m, 4H). LC-MS (m/z): 536.10 (M−H).

Workup

  1. customAfter complete consumption of starting material, reaction
  2. temperaturewas cooled to 0° C.
  3. additionfollowed by addition of pre
  4. customResulting
  5. customreaction mixture
  6. customAfter consumption of chloro intermediate, reaction mixture
  7. additionwas diluted with EtOAc (50 mL)
  8. washwashed with water (5×30 mL)
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated in vacuo
  11. customPurification
  12. washCompound was eluted

Sources & evidence

ORD record
ord-f194a570478d4a0a97c45208fb2587b5
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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