Water ethanol → HCID 67234001, compound

HRID 339684Notes

Reaction equation

HRID 339684 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:15])[CH:5]=[C:6]2[C:11]=1[N:10]=C(C(Br)Br)[CH:8]=[CH:7]2.[CH3:16][CH2:17][OH:18].[OH2:19]>CCO.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:3]=[C:4]([F:15])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:16]([C:17]([OH:19])=[O:18])[CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 19096565Water ethanolHCID 67234670HCID 67234670, compound

Product 1

HCID 67234001HCID 67234001, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

8-Bromo-2-(dibromomethyl)-6-fluoroquinoline (17.2 g, 43.2 mmol) was weighed into a flask and dissolved in 250 mL of EtOH, followed by addition of silver nitrate (23.5 g, 138 mmol) in 100 mL of 1:1 EtOH/H2O. The reaction was heated to reflux for 1 hour, at which time all starting material had been consumed. The reaction was removed from heat and filtered hot through a medium frit scintered glass funnel, affording 5.84 g of 8-bromo-6-fluoroquinoline-2-carboxylic acid as a white/yellow powder. The mother liquor was concentrated in vacuo, followed by extractive work-up (200 mL ethyl acetate/water). The combined organics were dried over Na2SO4 and concentrated in vacuo to afford the desired products as an orange-brown semi solid (99% overall; 6.4 g and 5.8 g respectively). MS APCI (+) m/z 298 and 300 (M+1 of each isotope) detected; MS APCI (−) m/z 268 and 269.9 (M−1 of each Br isotope) detected.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour, at which time all starting material
  3. customhad been consumed
  4. customThe reaction was removed
  5. temperaturefrom heat
  6. filtrationfiltered hot through a medium frit

Sources & evidence

ORD record
ord-f80f7f0b54a54aea8677e17af7caf940
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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