Water → 4-Bromo-2-iodophenol

HRID 2416136Notes

Reaction equation

HRID 2416136 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[I:9]N1C(=O)CCC1=O.S(=O)(=O)(O)O.O>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 78084-BromophenolHCID 120273N-Iodosuccinimide

Product 1

HCID 109245324-Bromo-2-iodophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Bromophenol (51.9 g, 0.30 mol) and N-iodosuccinimide (67.5 g, 0.30 mol) were combined in acetic acid (360 mL). The mixture was stirred briefly, treated with concentrated sulfuric acid (5 mL, 0.09 mol) and stirred at about 22° C. overnight. The mixture was poured into water (about 800 mL) with stirring to precipitate the product. The suspension was stirred for about 1 hour and filtered. The wet cake was washed with water (50 mL, 2×) and dried under reduced pressure at about 50° C. (80.9 g, 90%). MS-DEI (M+H)+ m/z at 298; 1H NMR (CDCl3 at 400 MHz) δ 5.28 (s,1H), 6.86 (d, 1H), 7.33 (dd, 1H), 7.75 (d, 1H); 13C NMR (CDCl3 at 100 MHz) δ 86.0, 112.8, 116.0, 132.7, 139.4, 153.7.

Workup

  1. stirringstirred at about 22° C. overnight
  2. stirringwith stirring
  3. customto precipitate the product
  4. stirringThe suspension was stirred for about 1 hour
  5. filtrationfiltered
  6. washThe wet cake was washed with water (50 mL, 2×)
  7. customdried under reduced pressure at about 50° C. (80.9 g, 90%)

Sources & evidence

ORD record
ord-58a62c047e01442199cbdd89bbc17cff
Source dataset
uspto-grants-2004_11
Patent number
US06822101B2

Reaction notes

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