tert-Butanol → tert-Butyl 2-bromobenzoate

HRID 1851875Notes

Reaction equation

HRID 1851875 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][C:12](O)([CH3:14])[CH3:13].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:12]([CH3:14])([CH3:13])[CH3:11])=[O:5]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 69402-Bromobenzoic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 3804415tert-Butyl 2-bromobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromobenzoic acid (8.08 g, 40.2 mmol), DMAP (0.492 g, 8.0 mmol) and t-BuOH (9.3 mL, 80.4 mmol) in dry DCM (300 mL) under argon, was added DCC (9.96 g, 48.2 mmol). The reaction mixture was stirred at room temperature for 20 h. The resulting mixture was filtered and the filtrate was evaporated in vacuo. The crude mixture was dissolved in AcOEt (300 mL) and washed with saturated aqueous NaHCO3 (261), brine and then dried over Na2SO4. After filtration, solvent was evaporated. The crude product was purified by flash chromatography on silica gel (AcOEt/hexane 0→30%) to obtain the title compound.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe crude mixture was dissolved in AcOEt (300 mL)
  4. washwashed with saturated aqueous NaHCO3 (261), brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration, solvent
  7. customwas evaporated
  8. customThe crude product was purified by flash chromatography on silica gel (AcOEt/hexane 0→30%)

Sources & evidence

ORD record
ord-e0b2abe4a4fa47c6b676ff110b76f216
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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