Hydrochloric Acid → 3-(7-bromo-2,3-dihydrobenzofuran-5-yl)propionic acid

HRID 324609Notes

Reaction equation

HRID 324609 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:12]2[O:11][CH2:10][CH2:9][C:8]=2[CH:7]=[C:6]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:5]=1.Cl>O1CCCC1>[Br:3][C:4]1[C:12]2[O:11][CH2:10][CH2:9][C:8]=2[CH:7]=[C:6]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10891878Ethyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate

Product 1

HCID 178269583-(7-bromo-2,3-dihydrobenzofuran-5-yl)propionic acidYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution (100 ml) of sodium hydroxide (15 g) was added to a tetrahydrofuran (20 ml) solution of ethyl 3-(7-bromo-2,3-dihydrobenzofuran-5-yl)propionate (19.1 g, 63.8 mmols), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was made acidic with hydrochloric acid added thereto, and this was then extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to obtain 12.8 g (yield: 73%) of the target compound.

Workup

  1. additionadded
  2. extractionthis was then extracted with ethyl acetate
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-644a545657094f9ead34f83a95c25feb
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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