Sodium Hydroxide → 5-Methyl-2-iodophenylacetyl chloride

HRID 2087032Notes

Reaction equation

HRID 2087032 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([I:14])=[C:8]([CH2:10][C:11](O)=[O:12])[CH:9]=1.S(Cl)([Cl:17])=O>CCO.O.C(Cl)Cl.CN(C=O)C>[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([I:14])=[C:8]([CH2:10][C:11]([Cl:17])=[O:12])[CH:9]=1

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 219386462-Iodo-5-methylbenzeneacetic acid

Product 1

HCID 219386685-Methyl-2-iodophenylacetyl chloride

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The nitrile (94.5 g, 0.37 mol) is dissolved in EtOH (350 ml) and treated with NaOH (29.4 g, 0.74 mol) which has been dissolved in water (200 ml). The reaction is heated to reflux temperature for 14 hours. After cooling to room temperature, ethanol is removed on a rotovap and 6N HCl added until the pH=1. The solid 5-methyl-2-iodophenylacetic acid is filtered off and washed with water (2×500 ml). After drying over P2O5 in a vacuum dessicator, the solid 5-methyl-2-iodophenyl acetic acid (mp 112-114°, 83 g, 0.30 mol) is dissolved in CH2Cl2 (450 ml) that contains several drops of DMF. To the solution thionyl chloride (32 ml, 0.450 mol) is added and the reaction heated to reflux temperature overnight. After cooling to room temperature, the reaction mixture is diluted with additional CH2Cl2 (500 ml) and washed with water (2×250 ml), saturated NaHCO3 (250 ml) and brine (250 ml). The solution is dried (MgSO4) and concentrated on a rotovap to give 5-methyl-2-iodophenylacetyl chloride as a yellowish oil.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux temperature for 14 hours
  3. customethanol is removed on a rotovap and 6N HCl
  4. additionadded until the pH=1
  5. filtrationThe solid 5-methyl-2-iodophenylacetic acid is filtered off
  6. washwashed with water (2×500 ml)
  7. dry with materialAfter drying over P2O5 in a vacuum dessicator
  8. temperaturethe reaction heated
  9. temperatureto reflux temperature overnight
  10. temperatureAfter cooling to room temperature
  11. washwashed with water (2×250 ml), saturated NaHCO3 (250 ml) and brine (250 ml)
  12. dry with materialThe solution is dried (MgSO4)
  13. concentrationconcentrated on a rotovap

Sources & evidence

ORD record
ord-89c9c7d3ea4b4138ba45e75bf78430ee
Source dataset
uspto-grants-2004_04
Patent number
US06727281B2

Reaction notes

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