Dichloromethane → tert-Butyl 2-bromobenzoate

HRID 475679Notes

Reaction equation

HRID 475679 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1CCC(N=C=NC2CCCCC2)CC1.C(Cl)Cl.[C:29](O)([CH3:32])([CH3:31])[CH3:30]>CN(C1C=CN=CC=1)C>[C:29]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Br:1])([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 64.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
0 °C

Procedure

2-Bromobenzoic acid (203.2 g, 1011 mmol) was added to a solution of 1.0 M DCC in DCM (1011 mL, 1011 mmol) and cooled at 0° C. DMAP (11.36 g, 93.0 mmol) and t-butyl alcohol (106.3 mL, 1112 mmol) were added and the mixture was stirred at room temperature for 10 minutes, then warmed to room temperature and stirred overnight. The mixture was then filtered, washed with saturated NaHCO3 (200 mL), saturated aqueous NaCl, dried over MgSO4, filtered and concentrated under reduced pressure to yield compound A as a clear oil (168.4 g).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. filtrationThe mixture was then filtered
  4. washwashed with saturated NaHCO3 (200 mL), saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92b0023c29d049388f558398c8237392
Source dataset
uspto-grants-2014_01
Patent number
US08637562B2

Reaction notes

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