Boron tribromide → 3-Ethyl-3-(3-hydroxy-phenyl)-azepan-2-one

HRID 1594857Notes

Reaction equation

HRID 1594857 reaction equation
B(Br)(Br)Br.[CH2:5]([C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:14])[CH3:6]>C(Cl)Cl>[CH2:5]([C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:14])[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 28154553-Ethyl-3-(3-methoxyphenyl)azepan-2-one

Product 1

HCID 217062193-Ethyl-3-(3-hydroxy-phenyl)-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of BBr3 (7.1 mL, 7.1 mmol) in CH2Cl2 was added to 3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one (as described in Step A above) (0.800 g, 0.323 mmol) dissolved in anhydrous CH2Cl2 (5 mL) at −78° C. After 48 h of stirring at room temperature, the reaction was quenched with H2O, extracted with CH2Cl2 (3×), dried (MgSO4), concentrated and purified using reverse phase chromatography (95/5-5/95 H2O/CH3CN with 0.1% TFA, flow=65 mL/min) to give the title compound.

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-493ef8c5f4894eeaa086fbd74133c8d7
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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