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Phenethyl bromide → HCID 9909367, compound

HRID 1636893
Notes
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Reaction equation

HRID 1636893 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:22])[CH:15]([F:21])[CH:16]([F:20])[C:17]([OH:19])=[O:18].C([N-]C(C)C)(C)C.[Li+].[CH2:31](Br)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:22])[CH:15]([F:21])[C:16]([F:20])([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:17]([OH:19])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 2724682Lithium diisopropylamideHCID 9796476HCID 9796476, compound

Product 1

HCID 9909367HCID 9909367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-dibenzofuran-2-yl-2,3-difluoro-4-oxo-butyric acid (1 equivalent, Example 6) in tetrahydrofuran cooled to -78° C. is added dropwise a solution of lithium diisopropylamide (2 equivalents). After stirring at -78° C. for 30 minutes, a solution of phenethyl bromide (1 equivalent) in tetrahydrofuran is added. The cooling bath is removed, and the reaction mixture gradually warms to room temperature and is stirred overnight. To this solution is added aqueous HCl (1 M) and ethyl acetate. The layers are separated, and the organic portion is washed with brine, dried (MgSO4), and concentrated in vacuo. The title compound is obtained by separation from the reaction by-product using silica gel chromatography (elution with chloroform/methanol).

Workup

  1. customThe cooling bath is removed
  2. customgradually warms to room temperature
  3. stirringis stirred overnight
  4. additionTo this solution is added aqueous HCl (1 M) and ethyl acetate
  5. customThe layers are separated
  6. washthe organic portion is washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4396593bd6f14b1181c32e54f53dcc04
Source dataset
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06037361

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes