Water → HCID 69099586, compound

HRID 2251565Notes

Reaction equation

HRID 2251565 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.[C:11]([O-:14])([O-])=[O:12].[Na+].[Na+].Br[CH2:18][C:19]([CH:21]1[CH2:23][CH2:22]1)=[O:20].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:7][C:8]([C:11]([O:14][CH2:18][C:19]([CH:21]2[CH2:23][CH2:22]2)=[O:20])=[O:12])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 69402-Bromobenzoic acidHCID 10340Sodium CarbonateHCID 109208412-Bromo-1-cyclopropylethan-1-one

Product 1

HCID 69099586HCID 69099586, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of bromobenzoic acid (9.97 g, 49.60 mmol) in DMF (65 mL) was added Na2CO3 (7.90 g, 74.54 mmol). After stirring for 15 min, 2-bromo-1-cyclopropylethanone (9.69 g, 59.44 mmol) was added, and the mixture was stirred at rt for 12 h. Water was added, and the mixture was extracted with Et2O (6×125 ml). The combined organic phases were dried with MgSO4 and concentrated in vacuo. Recrystallization from EtOH yielded 2-cyclopropyl-2-oxoethyl 4-bromobenzoate as white needles (8.53 g, 61%).

Workup

  1. stirringthe mixture was stirred at rt for 12 h
  2. extractionthe mixture was extracted with Et2O (6×125 ml)
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-d4a245ca7e4f42ac8080e4ac68702d28
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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