Chlorosuccinimide → HCID 58368557, compound

HRID 1192714Notes

Reaction equation

HRID 1192714 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, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

A solution of methyl 2-hydroxy-4-iodobenzoate (470 g, 1.7 mol) in acetic acid (1.9 L) was treated with N-chlorosuccinimide (250 g, 1.9 mol) and heated at 100-110° C. for 1 h. The reaction mixture was cooled to room temperature and the solid that precipitated was filtered, rinsed with acetic acid (250 mL) and water (2×500 mL), and dried on the filter under vacuum overnight to give the desired product (370 g, 70%) as a yellow powder. HPLC 95.8% pure @ 220 nm. LCMS for C8H7ClIO3 (M+H)+: m/z=312.9; Found: 313.0; 1H NMR (300 MHz, DMSO-d6): δ 10.5 (s, 1 H), 7.75 (s, 1 H), 7.57 (s, 1 H), 3.83 (s, 3 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solid that precipitated
  3. filtrationwas filtered
  4. washrinsed with acetic acid (250 mL) and water (2×500 mL)
  5. customdried on the
  6. filtrationfilter under vacuum overnight

Sources & evidence

ORD record
ord-ad8c34bcc4fa4a119772fa0fd0206c03
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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