Benzyl Bromide → HCID 21891956, compound

HRID 2304557Notes

Reaction equation

HRID 2304557 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:17]([CH:18]=[O:19])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:21])=[C:13]([OH:20])[CH:14]=2)[N:9]=1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([O:20][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[F:21])[N:9]=[C:8]([Cl:7])[C:17]([CH:18]=[O:19])=[CH:16]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21892040HCID 21892040, compound

Product 1

HCID 21891956HCID 21891956, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Potassium carbonate (9.2 g, 66 mmol) is added to a solution of 2-chloro-7-fluoro-6-hydoxy-3-quinolinecarbaldehyde (obtained according to 1.c, 13 g, 58 mmol) in anhydrous N,N-dimethylformamide (120 ml) and the mixture, placed under an argon atmosphere, is cooled down to 0° C. Benzyl bromide (7.9 ml, 66 mmol) is added dropwise and the reaction medium is maintained under agitation at ambient temperature for 16 hours. The reaction medium is then poured into ice cold water (200 ml) and the resulting yellow solid is filtered, then taken up in ethanol (200 ml) and concentrated under reduced pressure. The residue is taken up in ethyl ether (200 ml) and the resulting yellow solid is filtered then dried under reduced pressure in order to produce 15 g (82%) of a yellow solid, m.p. 228° C.

Workup

  1. temperaturethe reaction medium is maintained under agitation at ambient temperature for 16 hours
  2. filtrationthe resulting yellow solid is filtered
  3. concentrationconcentrated under reduced pressure
  4. filtrationthe resulting yellow solid is filtered
  5. customthen dried under reduced pressure in order

Sources & evidence

ORD record
ord-e1c5daaabefb431ea5f0d8310e37535d
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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