3,3-dibromoazepan-2-one → 3-Bromoazepan-2-one

HRID 845104Notes

Reaction equation

HRID 845104 reaction equation
[Br:1][C:2]1(Br)[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:9].C([O-])(=O)C.[Na+]>[Pd].C(O)(=O)C>[Br:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:9]

Participants

5

Reactant 2

HCID 2832713,3-dibromoazepan-2-oneHCID 517045Sodium Acetate

Product 1

HCID 110306353-Bromoazepan-2-oneYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 16 g (59 mmol) of 3,3-dibromoazacycloheptan-2-one, 150 ml of glacial acetic acid, 5.5 g (65 mmol) of sodium acetate, and 0.5 g of palladium on carbon (10%) was placed in a hydrogenator bottle and reduced under hydrogen at 30 psi. The mixture was filtered, and the filtrate distilled under vacuum to remove the acetic acid. The residue was neutralized with sat. Na2CO3, extracted into CH2Cl2, dried over MgSO4, and concentrated to yield 10.8 g (95%) of the product as an off-white solid; mp 109°-111° C.; NMR (CDCl3) 7.2 (1 H,m), 4.6 (1 H,m), 3.4 (2 H,m), 2.1 (4 H,m), 1.7 (2 H,m).

Workup

  1. filtrationThe mixture was filtered
  2. distillationthe filtrate distilled under vacuum
  3. customto remove the acetic acid
  4. extractionextracted into CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25bf50e80f6e45fda1bd047c8d1b1410
Source dataset
uspto-grants-1988_07
Patent number
US04755535

Reaction notes

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