Benzeneacetyl chloride, 4-bromo- → HCID 54374212, compound

HRID 735695Notes

Reaction equation

HRID 735695 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:27](=[O:28])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 181552Benzeneacetyl chloride, 4-bromo-HCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 54374212HCID 54374212, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask contained (R)-4-benzyl-2-oxazolidinone (800 mg, 4.51 mmol) in THF (10 mL), n-BuLi (2.83 mL, 1.6M, 4.52 mmol) was added at −78° C., dropwise. The solution was stirred at −78° C. for 10 min. A solution of 2-(4-bromophenyl)acetyl chloride (1.0 g, 4.28 mmol) in 10 mL THF was added. The solution was stirred −78° C. for 30 min, and rt for 3 h, and then was quenched with sat. NH4Cl and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4), and concentrated. Purification via flash chromatography (0-30% EtOAc in hexanes) gives 76A (1.29 g, 80%). MS (ESI) m/z 374.1 (M+H)+.

Workup

  1. customTo a round bottom flask contained
  2. stirringThe solution was stirred −78° C. for 30 min
  3. waitrt for 3 h
  4. customwas quenched with sat. NH4Cl
  5. extractionextracted with EtOAc (3×20 mL)
  6. washThe organic layer washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification via flash chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a5ca8cd86970422f82995b2c1cb828e2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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