Chlorosuccinimide → HCID 117720088, compound

HRID 1854585Notes

Reaction equation

HRID 1854585 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)C>[Cl:15][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][C:7]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acid

Product 1

HCID 117720088HCID 117720088, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

Dissolve 2-(3-isopropoxyphenyl)acetic acid (3.24 g, 16.6 mmol) in dimethylformamide (11.1 mL). Cool on an ice bath and add a solution N-chlorosuccinimide (2.44 g, 18.3 mmol) in dimethylformamide (12.2 mL). Stir overnight allowing the reaction to reach ambient temperature. Dilute the reaction mixture with diethyl ether. Wash with water. Extract the water wash with diethyl ether. Combine the diethyl ether extracts and wash with water and brine, dry over sodium sulfate, filter and concentrate under reduced pressure. Purify the residue by silica gel chromatography eluting with acetone: hexanes (0-25% gradient) to give the title compound (3.08 g, 13.47 mmol). MS (m/z): 245.8 (M+18).

Workup

  1. temperatureCool on an ice bath
  2. customthe reaction
  3. customto reach ambient temperature
  4. washWash with water
  5. extractionExtract the water
  6. washwash with diethyl ether
  7. washwash with water and brine
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. customPurify the residue by silica gel chromatography
  12. washeluting with acetone

Sources & evidence

ORD record
ord-37275310ce4148a38832a4e0447185cb
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

Loading…