Methanol → 2-Fluoro-3-iodo-4-methylbenzoic acid

HRID 2275418Notes

Reaction equation

HRID 2275418 reaction equation
[F:1][C:2]1[C:9]([I:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:3]=1C#N.S(=O)(=O)(O)[OH:13].[CH3:17][OH:18]>>[F:1][C:2]1[C:9]([I:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:3]=1[C:17]([OH:13])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 593838982-Fluoro-3-iodo-4-methylbenzonitrile

Product 1

HCID 593839002-Fluoro-3-iodo-4-methylbenzoic acid

Conditions

Temperature
115 °C

Procedure

To a 500 ml round bottom, three neck flask equipped with a condenser and magnetic stirrer, was added 2-fluoro-3-iodo-4-methyl-benzonitrile (33 g, 126.4 mmol), 70 ml of methanol, and 70 ml of 60% aqueous sulfuric acid. The flask was sealed and temperature was raised to 115° C. The reaction mixture was stirred at this temperature overnight. The precipitate that formed was filtered onto fritted filter, washed with 1 L of water, and dried under vacuum for 2 h and then in vacuum oven at 60° C. for 3 h to give 31.5 g of IXS-4-95-1. 1H NMR (DMSO-d6, 400 MHz) δ 13.2 (broad s, 1H), 7.74 (t, 1H), 7.26 (d, 1H), 2.47 (s, 3H), and MS [MH+]=280).

Workup

  1. customTo a 500 ml round bottom, three neck flask equipped with a condenser and magnetic stirrer
  2. customThe flask was sealed
  3. customThe precipitate that formed
  4. filtrationwas filtered onto fritted filter
  5. washwashed with 1 L of water
  6. customdried under vacuum for 2 h
  7. customin vacuum oven at 60° C. for 3 h to give 31.5 g of IXS-4-95-1

Sources & evidence

ORD record
ord-c274d762923748469f4ecfc590490726
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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