Sodium Carbonate → 1,3-Methanonaphthalen-4(1H)-one, 6-bromo-7-fluoro-2,3-dihydro-, oxime

HRID 575033Notes

Reaction equation

HRID 575033 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH:8]1[CH2:13][CH:6]([CH2:7]1)[C:5]2=O.C(=O)([O-])[O-].[Na+].[Na+].[NH2:21][OH:22].Cl>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH:8]1[CH2:13][CH:6]([CH2:7]1)[C:5]2=[N:21][OH:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86693064HCID 86693064, compound

Product 1

HCID 866930651,3-Methanonaphthalen-4(1H)-one, 6-bromo-7-fluoro-2,3-dihydro-, oximeYield 73.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
85 °C

Procedure

Into a 100-mL 3-necked round-bottom flask was placed a solution of 6-Bromo-7-fluoro-2,3-dihydro-1H-1,3-methano-naphthalen-4-one (4.5 g, 17.64 mmol, 1.00 equiv) in ethanol/H2O (20/20 mL), sodium carbonate (3.8 g, 35.85 mmol, 2.00 equiv), and NH2OH.HCl (2.4 g, 2.00 equiv). The resulting solution was stirred overnight at 85° C., cooled and concentrated under vacuum. The solids were collected by filtration, washed with 2×50 mL of water and dried to afford 3.5 g (73%) of 6-Bromo-7-fluoro-2,3-dihydro-1H-1,3-methano-naphthalen-4-one oxime as a white solid.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask was placed
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. filtrationThe solids were collected by filtration
  5. washwashed with 2×50 mL of water
  6. customdried

Sources & evidence

ORD record
ord-841abaaef6c54886bd661e84176c7f02
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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