1-Benzyl-3-bromobenzene → HCID 66577594, compound

HRID 1183376Notes

Reaction equation

HRID 1183376 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][N:30]=[C:29]([CH3:32])[C:28]=2[CH:33]=[O:34])=[CH:23][CH:22]=1>C1COCC1>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:33]([C:28]2[C:29]([CH3:32])=[N:30][O:31][C:27]=2[C:24]2[CH:25]=[CH:26][C:21]([Br:20])=[CH:22][CH:23]=2)[OH:34])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5975321-Benzyl-3-bromobenzeneHCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 66577594HCID 66577594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-Benzyl-3-bromo-benzene (0.811 g, 3.3 mmol) was dissolved in THF (2 mL), cooled to −78° C. and then n-butyllithium (2.0 M in THF, 1.65 mL, 3.3 mmol) was added dropwise. The reaction was stirred for 15 minutes then warmed to 0° C. and 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (1.05 g, 3.96 mmol) was added. The reaction was allowed to warm to room temperature while stirring for 1 hour. The reaction was quenched with aqueous ammonium chloride then submitted to standard aqueous workup and silica gel chromatography to give the title compound.

Workup

  1. temperaturethen warmed to 0° C.
  2. temperatureto warm to room temperature
  3. stirringwhile stirring for 1 hour
  4. customThe reaction was quenched with aqueous ammonium chloride

Sources & evidence

ORD record
ord-f966a10fa9554c16b2ce4d1897357683
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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