Water → Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate

HRID 385030Notes

Reaction equation

HRID 385030 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[I:16]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O.O>ClCCl.CO>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([I:16])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

Product 1

HCID 12084815Methyl 3-t-butyl-4-hydroxy-5-iodobenzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 3-t-butyl-4-hydroxybenzoate (1.83 g) was dissolved in dichloromethane (24 mL) and methanol (3 mL), and N-iodosuccinimide (2.08 g) and trifluoromethanesulfonic acid (3 mL) were added to the solution, and then the mixture was stirred at room temperature for 15 minutes. Water was added to the reaction solution, and then the organic layer was separated. The organic layer was washed with 10% sodium thiosulfate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.77 g) as a brown crystal.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with 10% sodium thiosulfate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5c22d3a8a061459990ebdc6a40e1ca1c
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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