N-bromobutanimide → HCID 131734532, compound

HRID 591533Notes

Reaction equation

HRID 591533 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH2:6]1.[Br:16]N1C(=O)CCC1=O>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C@H:5]1[C:9]2[CH:10]=[C:11]([Br:16])[C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 131734532HCID 131734532, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl((3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate (10 g) in THF (dry) (192 mL) was added N-bromosuccinimide (8.55 g) at 0° C. The mixture was gradually warmed to room temperature and stirred at room temperature for 1.5 day. The mixture was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (13.78 g).

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-8da3a5501eef44f393ded531f745efb6
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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