1,3-Dibromopropane → HCID 67145241, compound

HRID 711600Notes

Reaction equation

HRID 711600 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 67145241HCID 67145241, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-(4-hydroxyphenyl)propan-2-one (1 g, 6.67 mmol), 1,3-dibromopropane (0.74 mL, 7.3 mmol) and potassium carbonate (1.84 g, 13 3 mmol) in 2-butanone (30 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic phase was separated, and the aqueous phase was extracted with additional ethyl acetate. The organic extracts were combined, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue obtained was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 2.14 (s, 3H), 2.36-2.27 (m, 2H), 3.60 (t, J=6.4 Hz, 2H), 3.63 (s, 2H), 4.09 (t, J=5.8 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 7.11 (d, J=8.7 Hz, 2H); MS (DCI/NH3) m/z 288 (M+NH4)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. custompartitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with additional ethyl acetate
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue obtained
  11. customwas chromatographed on silica gel eluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5c1b17984ea24fa391e0438d2c255153
Source dataset
uspto-grants-2015_11
Patent number
US09181275B2

Reaction notes

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