Boron tribromide → 3-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one

HRID 1594852Notes

Reaction equation

HRID 1594852 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:14]2=[O:20])[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:14]2=[O:20])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12875111Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one

Product 1

HCID 126655233-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of BBr3 (1.0 mL, 1.00 mmol) in CH2Cl2 was added to 3-(3-methoxy-phenyl)-azepan-2-one (as described in Step B above) (0.200 g, 0.912 mmol) dissolved in anhydrous CH2Cl2 (5 mL) at −78° C. After 30 hr of stirring at RT, 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-1835112443054888bf73676cfe51e335
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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