Sulfuric Acid → tert-Butyl 4-bromo-3-methoxybenzoate

HRID 1908102Notes

Reaction equation

HRID 1908102 reaction equation
[O-]S([O-])(=O)=O.[Mg+2].OS(O)(=O)=O.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[O:22][CH3:23].[CH3:24][C:25](O)([CH3:27])[CH3:26]>C(Cl)Cl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][C:25]([CH3:27])([CH3:26])[CH3:24])=[O:18])=[CH:15][C:14]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 25307097tert-Butyl 4-bromo-3-methoxybenzoateYield 13.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

MgSO4 (4.82 g, 40.0 mmol), DCM (40 mL), and H2SO4 (533 μL, 10.0 mmol) were combined at 0° C. and the mixture was allowed to stir for 30 minutes at 0° C. 4-Bromo-3-methoxy-benzoic acid (2.31 g, 10.0 mmol) and 2-methylpropan-2-ol (4.78 mL, 50.0 mmol) were added and the mixture was allowed to stir at rt overnight. The mixture was filtered to remove the MgSO4 and the filtrate was washed with 1N NaOH. The layers were separated and the organic layer was dried over sodium sulfate and the solvent was removed to yield 400 mg of tert-butyl 4-bromo-3-methoxybenzoate. ESI-MS m/z calc. 286.0. found 287.0 (M+1)+; Retention time: 3.11 minutes (4 min run).

Workup

  1. customwere combined at 0° C.
  2. stirringto stir at rt overnight
  3. filtrationThe mixture was filtered
  4. customto remove the MgSO4
  5. washthe filtrate was washed with 1N NaOH
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-7259f1ec15464356898776b768ce5a04
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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