Bromine → Ethyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate

HRID 324608Notes

Reaction equation

HRID 324608 reaction equation
[Br:1]Br.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][C:6]=2[CH2:5][CH2:4]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:8]1[C:7]2[O:3][CH2:4][CH2:5][C:6]=2[CH:11]=[C:10]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 11053175Ethyl 3-(2,3-dihydrobenzofuran-5-yl)propanoate

Product 1

HCID 10891878Ethyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoateYield 97.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (10.5 g, 65.8 mmols) was dropwise added to an acetic acid (150 ml) solution containing ethyl 3-(2,3-dihydrobenzofuran-5-yl)propionate (14.5 g, 65.8 mmols) and sodium acetate (5.94 g, 72.4 mmols), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Water was added to the residue, which was then extracted with ethyl acetate. The extract was washed with a saturated saline solution and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure to obtain 19.2 g (yield: 97%) of the target compound. This was oily.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater was added to the residue, which
  4. extractionwas then extracted with ethyl acetate
  5. washThe extract was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-34afec7ce78f41ecbe5033eeb6c46bf8
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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