Bromine → 1-Bromo-2-iodo-4,5-dimethoxybenzene

HRID 1165466Notes

Reaction equation

HRID 1165466 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Br:12]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[Br:12][C:7]1[CH:6]=[C:5]([O:8][CH3:9])[C:4]([O:10][CH3:11])=[CH:3][C:2]=1[I:1]

Participants

6

Reactant 3

HCID 24408Bromine2×HCID 2303074-Iodo-1,2-dimethoxybenzeneHCID 23665763Sodium Bisulfite

Product 1

HCID 33464041-Bromo-2-iodo-4,5-dimethoxybenzeneYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

4-Iodoveratrole (26.0 g, 0.0985M) in acetic acid (25 ml) was treated with bromine (6.5 ml, 0.127M) in acetic acid (30 ml) and stirred at room temperature for one hour. The mixture was diluted with water (300 ml) and treated with sodium bisulfite to discharge the excess bromine. The white solid was filtered, washed with water and dried in vacuo over P2O5 to give 4-bromo-5-iodoveratrole (33.0 g, 95% yield) as a white solid, mp 98°-100° C. (literature: Baker et al., J. Chem. Soc. 3986 (1961), mp 102°-104° C.). NMR (CDCl3) δ 3.83 ppm (s, 6H, (2x) OCH3), 7.06 (s, 1H, ArH), 7.21 (s, 1H, ArH).

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with water
  3. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-ec6178f1dbfa4a42b8c30e2230e03b8e
Source dataset
uspto-grants-1990_03
Patent number
US04910198

Reaction notes

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