Dichloromethane → tert-Butyl 2-bromobenzoate

HRID 1810123Notes

Reaction equation

HRID 1810123 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-c6f3433ce62746beb819243a075ed3c5
Source dataset
uspto-grants-2013_01
Patent number
US08362061B2

Reaction notes

Loading…