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4-Benzyloxybenzyl chloride → 2-(2-(4-Benzyloxy-phenyl)-ethyl]-6,7-difluoro-quinoline

HRID 226264
Notes
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Reaction equation

HRID 226264 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.C([N-]C(C)C)(C)C.[Li+].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Cl)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][CH2:13][C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([F:12])=[C:2]([F:1])[CH:3]=3)[N:8]=2)=[CH:34][CH:35]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 700424-Benzyloxybenzyl chlorideHCID 2724682Lithium diisopropylamideHCID 222413776,7-Difluoro-2-methylquinoline

Product 1

HCID 577544362-(2-(4-Benzyloxy-phenyl)-ethyl]-6,7-difluoro-quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 8.9 g (49.6 mmol) of the product from Example 1, step 3 in 90 ml THF is cooled at −50° C. 28.6 ml (57.2 mmol) of a 2M solution of lithium diisopropylamide are added and the solution is allowed to heat to −10° C. After 15′ stirring at this temperature the deep colored solution is again cooled to −50° C. A solution of 11.6 g (49.8 mmol) of 1-benzyloxy-4-chloromethyl-benzene in 60 ml THF is dropped into the cooled solution. The system is allowed to heat to room temperature and stirred overnight. The solvent is evaporated and the residue that solidifies on cooling is stirred with ethyl ether and filtered. The residue is filtered through SiO2 eluting with dichloromethane. The yield is 3.75 g (20%).

Workup

  1. temperatureis again cooled to −50° C
  2. temperatureto heat to room temperature
  3. stirringstirred overnight
  4. customThe solvent is evaporated
  5. temperatureon cooling
  6. stirringis stirred with ethyl ether
  7. filtrationfiltered
  8. filtrationThe residue is filtered through SiO2 eluting with dichloromethane

Sources & evidence

ORD record
ord-ca395e8fb5b7438997f54e1087e83bcd
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07557212B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes