Bromine → HCID 70001611, compound

HRID 1635566Notes

Reaction equation

HRID 1635566 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([CH:6]([CH3:15])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])[CH3:5].[Br:16]Br>C(O)(=O)C>[CH3:1][CH2:2][CH2:3][CH:4]([C:6]([Br:16])([CH3:15])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])[CH3:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 70001019HCID 70001019, compound

Product 1

HCID 70001611HCID 70001611, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the ketone 3 (5.03 g, 0.025 mol) in 15 ml of glacial acetic acid, Br2 (3.94 g, 0.025 mol) was added dropwise, with stirring at 0° C. After the addition was complete the ice bath was removed and the solution was stirred for 2 h at 23° C. The reaction mixture was quenched by the addition of water and after cooling it was extracted with ether. After drying and concentration under vacuum, the residue was purified by flash chromatography, eluting with hexanes, to afford 5.0 g (72%) of compound 4. 1H NMR (100 MHz, CDCl3) δ 0.8 (t, 3H), 1.4 (m, 6H), 1.8 (d, J=6.5 Hz, 3H), 2.7 (t, J=6.4 Hz, 2H), 5.25 (q, 1H), 7.25 (d, J=8.0 Hz, 2H), 7.9 (d, J=8.2 Hz, 2H).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. stirringthe solution was stirred for 2 h at 23° C
  4. customThe reaction mixture was quenched by the addition of water
  5. temperatureafter cooling it
  6. extractionwas extracted with ether
  7. customAfter drying
  8. concentrationconcentration under vacuum
  9. customthe residue was purified by flash chromatography
  10. washeluting with hexanes

Sources & evidence

ORD record
ord-4a5ef48e69ef40d3bf943f9d2377c30e
Source dataset
uspto-grants-2003_01
Patent number
US06509367B1

Reaction notes

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