4-bromo-N,N-diethyl-2-[(2R)-2-hydroxypropyl]benzamide → (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one

HRID 2173416

Reaction equation

HRID 2173416 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6](N(CC)CC)=[O:7])=[C:4]([CH2:15][C@H:16]([OH:18])[CH3:17])[CH:3]=1>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:13][CH:14]=1)[C:6](=[O:7])[O:18][C@H:16]([CH3:17])[CH2:15]2

Participants

4

Reactant 1

HCID 866930334-bromo-N,N-diethyl-2-[(2R)-2-hydroxypropyl]benzamide

Product 1

HCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-bromo-N,N-diethyl-2-[(2R)-2-hydroxypropyl]benzamide (12.2 g, 38.8 mmol) dissolved in 4N HCl in Dioxane (200 mL) was stirred at room temperature and monitored by tlc. After 3 days the reaction was partitioned between EtOAc (300 mL) and water (300 mL). The aqueous phase was further extracted with EtOAc (2×250 mL). The combined organic layers were then washed with water (200 mL), brine (200 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was then purified via MPLC (15-30% EtOAc/Hexane) to afford (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one.

Workup

  1. customAfter 3 days the reaction was partitioned between EtOAc (300 mL) and water (300 mL)
  2. extractionThe aqueous phase was further extracted with EtOAc (2×250 mL)
  3. washThe combined organic layers were then washed with water (200 mL), brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was then purified via MPLC (15-30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-3c04e482e78148dea07a0d263a539a6a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Linked notes

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