Boron tribromide → HCID 21706255, compound

HRID 1594922Notes

Reaction equation

HRID 1594922 reaction equation
B(Br)(Br)Br.[CH3:5][C:6]1([CH:14]2[NH:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=[C:8]([O:12]C)[CH2:7]1>C(Cl)(Cl)Cl>[CH3:5][C:6]1([CH:14]2[NH:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH2:7]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21706269HCID 21706269, compound

Product 1

HCID 21706255HCID 21706255, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

BBr3 (1M in CH2Cl2) (1 mL, 1 mmol) was added dropwise to a solution of 7-(1-methyl-3-methoxyphenyl)-azepan-2-one, as described in Step D above, (0.06 g, 0.26 mmol) in CHCl3 (1 mL) at 0° C. with stirring. The ice bath was removed and stirring was continued for 1 h. The reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL), the organic layer separated, washed with H2O, dried (MgSO4), filtered and concentrated to give the title compound after SiO2 chromatography (CHCl3:MeOH, 10:1).

Workup

  1. customat 0° C.
  2. customThe ice bath was removed
  3. stirringstirring
  4. customThe reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL)
  5. customthe organic layer separated
  6. washwashed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ba9941c0c4ea4de9add891c79c61b6a5
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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