Bromine → HCID 25143348, compound

HRID 1894784Notes

Reaction equation

HRID 1894784 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[Br:13]Br>CO>[Br:13][CH2:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 10515164-(4-BROMOPHENYL)-2-BUTANONE

Product 1

HCID 25143348HCID 25143348, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-(4-bromophenyl)-2-butanone (1 mmol) in methanol (8 mL) stirred at room temperature, a solution of bromine (160 mg, 51.6 μL, 1 mmol) in methanol (1 mL) was added in one portion. The orange reaction mixture was then stirred at room temperature for 2 h, and, after the starting material had been consumed (TLC monitoring, hexanes-ethyl acetate 4:1 v/v), the reaction was quenched by adding a 0.3 M sodium thiosulfate solution (618 μL), and diluted with ethyl acetate (15 mL). The resulting mixture was washed with water (15 mL), the organic layer was separated, and the aqueous layer was extracted further with ethyl acetate (3×15 mL). The combined organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure to give a residue that was chromatographed on a silica gel column using hexanes-ethyl acetate (15:1 v/v) as mobile phase to give 1-bromo-4-(4-bromophenyl)-2-butanone as a white solid (193 mg, 63%): mp 63-64° C., Rf=0.42 (hexanes-ethyl acetate 4:1 v/v); 1H NMR (400 MHz, CDCl3): δ 2.89 (t, J=6.8 Hz, 2H). 2.96 (t, J=6.8 Hz, 2H), 3.84 (s, 2H), 7.07 (d, J=8 Hz, 2H), 7.41 (d, J=8 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ 29.3, 34.3, 41.2, 120.2, 130.2, 131.7, 139.4, 201.0; HRMS (EI) Calcd. for C10H10Br2O: 303.9098 (M+). Found: 303.9090.

Workup

  1. customafter the starting material had been consumed (TLC monitoring, hexanes-ethyl acetate 4:1 v/v)
  2. customthe reaction was quenched
  3. additionby adding a 0.3 M sodium thiosulfate solution (618 μL)
  4. additiondiluted with ethyl acetate (15 mL)
  5. washThe resulting mixture was washed with water (15 mL)
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted further with ethyl acetate (3×15 mL)
  8. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue that
  11. customwas chromatographed on a silica gel column

Sources & evidence

ORD record
ord-0abb7e0c7cd14c8c8ac835e24e8051c8
Source dataset
uspto-grants-2013_08
Patent number
US08513294B2

Reaction notes

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