Sulfuric Acid → N-(2-(4-Bromophenyl)propan-2-YL)acetamide

HRID 76161Notes

Reaction equation

HRID 76161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[OH:12]S(O)(=O)=O.[C:17](#[N:19])[CH3:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:19][C:17](=[O:12])[CH3:18])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 126819202-(4-Bromophenyl)propan-2-ol

Product 1

HCID 39616691N-(2-(4-Bromophenyl)propan-2-YL)acetamide

Procedure

To 21.0 g (97.6 mmol) 2-(4-bromophenyl)-propan-2-ol in 1 L ACN are added 16.1 mL conc. H2SO4 dropwise while keeping the temperature at 20° C. The resulting mixture is stirred at r.t. over night. The solvent is removed in vacuo and the residue is partitioned between water and diethylether. The organic layer is washed with water (2×), sat. aq. NaHCO3 solution (2×) and water again (1×). The solution is dried with MgSO4 and the solvent is removed in vacuo. The crude product is triturated with PE.

Workup

  1. customat 20° C
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between water and diethylether
  4. washThe organic layer is washed with water (2×), sat. aq. NaHCO3 solution (2×) and water again (1×)
  5. dry with materialThe solution is dried with MgSO4
  6. customthe solvent is removed in vacuo
  7. customThe crude product is triturated with PE

Sources & evidence

ORD record
ord-a749d125b04e4af1b21bf3151fe5dd09
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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