Dichloromethane → tert-Butyl 2-bromobenzoate

HRID 1517749Notes

Reaction equation

HRID 1517749 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-938ef347a3ce413e9f33f3280b83aa8f
Source dataset
uspto-grants-2012_07
Patent number
US08232306B2

Reaction notes

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