3-Bromoanisole → 4-Bromo-2-methoxybenzene-1-sulfonyl chloride

HRID 130417Notes

Reaction equation

HRID 130417 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[Cl:10][S:11](O)(=[O:13])=[O:12]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:11]([Cl:10])(=[O:13])=[O:12])=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

3

Reactant 2

HCID 169713-BromoanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 187549524-Bromo-2-methoxybenzene-1-sulfonyl chloride

Conditions

Temperature
0 °C

Procedure

To chlorosulfonic acid (20 ml) at 0° C. was added dropwise 3-bromoanisole (18.7 g, 0.1 mol) at such a rate that the internal temperature remained below 5° C. The mixture was stirred at 0° C. for 1 hour and added dropwise to crushed ice. The mixture was extracted with ethyl acetate and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:25 ethyl acetate:pentane) to afford the title compound; 4-bromo-2-(methyloxy)benzenesulfonyl chloride (D30) 1H-NMR (CDCl3) δ 7.81 (1H, d, J 8 Hz), 7.28 (1H, d, J 2 Hz), 7.26 (1H, dd, J 8, 2 Hz), 4.07 (3H, s) and an isomer; 2-bromo-4-(methyloxy)benzenesulfonyl chloride 1H-NMR (CDCl3) δ 8.12 (1H, d), 7.33 (1H, d), 6.97 (1H, dd), 3.92 (3H, s).

Workup

  1. customremained below 5° C
  2. additionadded dropwise
  3. customto crushed ice
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (1:25 ethyl acetate:pentane)

Sources & evidence

ORD record
ord-203f0475cad0465b95fc7f337c0a8c19
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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