Dichloromethane → tert-Butyl 2-bromobenzoate

HRID 1517737Notes

Reaction equation

HRID 1517737 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C(Cl)Cl.[Br:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].[C:29](O)([CH3:32])([CH3:31])[CH3:30]>CN(C1C=CN=CC=1)C>[C:29]([O:23][C:22](=[O:24])[C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[Br:19])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 69402-Bromobenzoic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 3804415tert-Butyl 2-bromobenzoateYield 101.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of DCC (32.8 g, 159 mmol) in DCM (200 mL, 2 mol) was added 2-bromobenzoic acid (32.0 g, 159 mmol) followed by DMAP (1.8 g, 15 mmol) and t-butyl alcohol (15.2 mL, 159 mmol). The mixture was stirred at room temperature for 16 hours, then filtered. The organic was washed with saturated NaHCO3 (200 mL), saturated aqueous NaCl, dried over MgSO4, filtered and concentrated under reduced pressure to yield compound A as an oil (41.6 g).

Workup

  1. filtrationfiltered
  2. washThe organic was washed with saturated NaHCO3 (200 mL), saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a00830da01094fbea2d008466b5b52fa
Source dataset
uspto-grants-2012_07
Patent number
US08232306B2

Reaction notes

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