Chlorosuccinimide → HCID 58368557, compound

HRID 515840Notes

Reaction equation

HRID 515840 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 61.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 2-hydroxy-4-iodobenzoate (50 g, 0.18 mol) [Aldrich, 652636] in acetic acid (360 mL) was treated with N-chlorosuccinimide (29 g, 0.22 mol) and heated at 100° C. for 1 hour. The reaction mixture was cooled until the internal temperature was 19° C. and then the solid that precipitated was filtered, washed with cold acetic acid, and air dried. The solid was diluted with toluene and concentrated (2×200 mL) to remove residual acetic acid to give 34.8 g of the desired product. The filtrate was concentrated, and the residue was purified by flash column chromatography using ethyl acetate in hexanes (0%-20%) to give an additional 8.6 g of desired product (total yield=43 g, 77%). LCMS for C8H7ClIO3 (M+H)+: m/z=312.9; Found: 313.0.

Workup

  1. temperatureThe reaction mixture was cooled until the internal temperature
  2. customwas 19° C.
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with cold acetic acid, and air
  6. customdried
  7. additionThe solid was diluted with toluene
  8. concentrationconcentrated (2×200 mL)
  9. customto remove residual acetic acid

Sources & evidence

ORD record
ord-4fc4403e34a048b297d629f4e4b7aa19
Source dataset
uspto-grants-2015_08
Patent number
US09108984B2

Reaction notes

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