Sulfuric Acid → Tert-butyl 2-bromo-2-phenylacetate

HRID 1771035Notes

Reaction equation

HRID 1771035 reaction equation
S(=O)(=O)(O)O.[O-]S([O-])(=O)=O.[Mg+2].[Br:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([OH:16])=[O:15].[C:23](O)([CH3:26])([CH3:25])[CH3:24].C([O-])(O)=O.[Na+]>ClCCl.O>[Br:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([O:16][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:15]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 97919Bromo(phenyl)acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11000147Tert-butyl 2-bromo-2-phenylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Concentrated sulphuric acid (0.55 mL; 10 mmol) was added to a stirred suspension of anhydrous MgSO4 (4.8 g; 40 mmol) in dry dichloromethane (40 mL) at ambient temperature. After 15 min stirring, α-bromophenylacetic acid (2.15 g; 10.0 mmol) was added, followed by t-butyl alcohol (4.8 mL; 50 mmol). The reaction flask was closed with a stopper and the mixture was stirred 7 days at ambient temperature. Saturated NaHCO3 solution (75 mL) and water (75 mL) was added to the reaction mixture. After separating, the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organic layers were washed with water and dried (MgSO4). After filtration and evaporation 2.39 g (88%) product was obtained (colourless oil).

Workup

  1. customThe reaction flask was closed with a stopper
  2. stirringthe mixture was stirred 7 days at ambient temperature
  3. customAfter separating
  4. extractionthe aqueous layer was extracted with dichloromethane (2×15 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration
  8. customevaporation 2.39 g (88%) product
  9. customwas obtained (colourless oil)

Sources & evidence

ORD record
ord-8bf1bbbc132743c2ac983445f8e268c2
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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