Water → 1-(5-Chloro-3-iodo-2-methoxy-4-methylphenyl)ethanone

HRID 1499668Notes

Reaction equation

HRID 1499668 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]([CH3:19])=[C:10]([I:18])[C:11](O)=[C:12]([C:14](=[O:16])[CH3:15])[CH:13]=1.CI.O>CN(C)C=O>[Cl:7][C:8]1[C:9]([CH3:19])=[C:10]([I:18])[C:11]([O:4][CH3:1])=[C:12]([C:14](=[O:16])[CH3:15])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 114723941-(5-Chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone

Product 1

HCID 866667971-(5-Chloro-3-iodo-2-methoxy-4-methylphenyl)ethanoneYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (72.4 g, 524 mmol) was added to a mixture of 1-(5-chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone (81.3 g, 262 mmol) and methyl iodide (19.6 mL, 314 mmol) in N,N-dimethylformamide (250 mL). The mixture was stirred at room temperature for 4 hours. Water (500 mL) was added and stirred for 15 minutes. The dark solids were filtered and dried in vacuo to give 42.3 g of the desired product. The filtrate was extracted with EtOAc (4×). The combined filtrates were washed with water (2×) and brine, dried (MgSO4), filtered and concentrated. The solids were dried in vacuo to give an additional 37.2 g of the desired product. The product was used without further purification, LCMS calculated for C10H11ClIO2 (M+H)+: m/z=324.9; Found: 325.0. 1H NMR (300 MHz, CDCl3): δ 7.62 (s, 1H), 3.78 (s, 3H), 2.65 (s, 3H), 2.62 (s, 3H) ppm.

Workup

  1. stirringstirred for 15 minutes
  2. filtrationThe dark solids were filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-09a819075248471f87d4c1702b200f34
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…