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

HRID 2250658Notes

Reaction equation

HRID 2250658 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 powdered 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-1e792961175147feb79eb586bcfcc0ae
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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