Water → HCID 86617919, compound

HRID 1698709Notes

Reaction equation

HRID 1698709 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:15]([CH:16]=[O:17])=[C:14]([OH:18])[C:13]([O:19][CH3:20])=[CH:12][CH:11]=1.O.C(OCC)(=O)C>C(#N)C>[Br:1][C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([OH:18])=[C:15]([C:10]=1[F:9])[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 224828186-Fluoro-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 86617919HCID 86617919, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding 3.11 g of N-bromosuccinimide to a solution of 2.98 g of 6-fluoro-2-hydroxy-3-methoxybenzaldehyde [CAS No. 457628-15-8] in 15 ml of acetonitrile, the mixture was stirred overnight at room temperature. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give 3.13 g of 5-bromo-6-fluoro-2-hydroxy-3-methoxybenzaldehyde (crude product).

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationThe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f40419d66a42465d87acbe5f002b442f
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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