Sulfuric Acid → 1,1-Dimethylethyl 3-bromo-5-iodobenzoate

HRID 860513Notes

Reaction equation

HRID 860513 reaction equation
[O-]S([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([I:22])[CH:21]=1)[C:16]([OH:18])=[O:17].[C:23](O)([CH3:26])([CH3:25])[CH3:24]>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([I:22])[CH:21]=1)[C:16]([O:18][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 574859731,1-Dimethylethyl 3-bromo-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigirously stirred suspension of poudered MgSO4 (7.36 g) in dichloromethane (50 mL) was added sulfuric acid (0.758 mL) at room temperature. After stirring for 15 minutes, to the mixture was added 3-bromo-5-iodobenzoic acid (5.00 g) followed by tert-butanol (7.31 mL). The mixture was stirred for 3 days at room temperature. The mixture was partitioned between EtOAc and water. The organic layer was washed with satd. NaHCO3 and brine, dried over MgSO4, and evaporated to give tert-butyl 3-bromo-5-iodobenzoate as pale purple crystals (4.44 g).

Workup

  1. stirringThe mixture was stirred for 3 days at room temperature
  2. customThe mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with satd
  4. dry with materialNaHCO3 and brine, dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-4379f2da7117478fa21c023fc4202869
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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