4-Phenyl-3-Buten-2-one → HCID 54027402, compound

To a solution of styryl methyl ketone (5.0 g, 34.2 mmol) in dry THF (80 mL) at room temperature under nitrogen is slowly added a solution of pyrrolidone hydrotribromide (20.3 g, 40.9 mmol) in dry THF (120 mL) in 1 hr. The mixture is continued to stir at room temperature for 24 hrs. Excess pyrrolidone hydrotribromide is removed by filtration. The filtrate is concentrated to dryness. The resulting residue is dissolved in Et2O, washed with brine and dried (Na2SO4). Removal of the solvents affords a crude product, which is chromatographed on silica gel eluting with Et2O-hexanes (1:6) to give bromomethyl styryl ketone (5.91 g, 77%) as colorless crystals (from Et2O), 1H NMR (400 MHz, CDCl3) d 7.70 (1H, d, J=16.0 Hz, β-CH═), 7.58 (2H, m, Ph), 7.43 (3H, m, Ph), 6.95 (1H, d, J=16.0 Hz, a-CH═), 4.11 (2H, s, CH2Br); 13C NMR (100 MHz, CDCl3) d 191.1 (s, C═O), 145.4 (d, β-CH═), 134.0 (s, Ph), 131.2 (d, Ph), 129.1 (2C, d, Ph), 128.7 (2C, d, Ph), 122.3 (d, a-CH═), 33.3 (t, CH2Br).

1. customExcess pyrrolidone hydrotribromide is removed by filtration
2. concentrationThe filtrate is concentrated to dryness
3. dissolutionThe resulting residue is dissolved in Et2O
4. washwashed with brine
5. dry with materialdried (Na2SO4)
6. customRemoval of the solvents
7. customaffords a crude product, which
8. customis chromatographed on silica gel eluting with Et2O-hexanes (1:6)

ORD record

ord-6be6c116145846bb8892a57c5ac71ffc

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109380B2