Chlorosuccinimide → HCID 58368557, compound

HRID 1192696Notes

Reaction equation

HRID 1192696 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:13][C:9]1[C:10]([I:12])=[CH:11][C:2]([OH:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 58368557HCID 58368557, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-hydroxy-4-iodobenzoate (10.0 g, 36.0 mmol, from Aldrich) and N-chlorosuccinimide (5.76 g, 43.2 mmol) in acetic acid (40 mL) was heated at 100° C. for 1 hour and then cooled to room temperature overnight. The precipitate was collected by filtration and washed with ethyl acetate and then air dried to give the desired product. In addition, the filtrate was concentrated to dryness and partitioned between water and ethyl acetate. The organic phase was separated, washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to give additional desired product (total 9.03 g, 82%). LCMS calculated for C8H7ClIO3 (M+H)+: m/z=312.9; Found: 313.0.

Workup

  1. temperaturecooled to room temperature overnight
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethyl acetate
  4. customair dried

Sources & evidence

ORD record
ord-f54fb4a26cfc43b0820afc7ce4fafaff
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…