2,6-Dichlorophenol → 2,6-dichloro-4-iodophenol

HRID 526777Notes

Reaction equation

HRID 526777 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].C1C(=O)N([I:17])C(=O)C1>CO>[Cl:1][C:2]1[CH:7]=[C:6]([I:17])[CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 68992,6-DichlorophenolHCID 120273N-Iodosuccinimide

Product 1

HCID 44930832,6-dichloro-4-iodophenolYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,6-dichlorophenol (10 g, 61.35 mmol, 1.00 equiv) and NIS (27.6 g, 245.33 mmol, 2.00 equiv) in methanol (100 mL) was stirred for 1 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was redissolved in 50 mL of ethyl acetate and washed with 3×30 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with petroleum ether (100%) to give 10.5 g (59%) of 2,6-dichloro-4-iodophenol as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 9.83 (s, 1H), 7.27 (s, 2H) ppm.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutionThe residue was redissolved in 50 mL of ethyl acetate
  3. washwashed with 3×30 mL of brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified on a silica gel column
  7. washeluted with petroleum ether (100%)

Sources & evidence

ORD record
ord-5f35dcd81a244aa39084e20a0fef2a79
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

Loading…