1,3-Dibromopropane → 1-(3-Bromopropyl)-4-phenoxybenzene

HRID 459266Notes

Reaction equation

HRID 459266 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Br:15][CH2:16][CH2:17][CH2:18][C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 132544-Phenoxyphenol

Product 1

HCID 155954721-(3-Bromopropyl)-4-phenoxybenzeneYield 87.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
22 °C

Procedure

To a 22 L flask was added 4-phenoxyphenol (900 g), 1,3-dibrompropane (5858 g), powered potassium carbonate (1335 g), and methyl ethyl ketone (9 L). The mixture was stirred for 30 minutes at 22° C. The off-white slurry was heated to a gentle reflux (˜83° C.) and held at that temperature for 16 hours. The off white slurry was cooled to 25° C. and vacuum filtered, washing the cake of inorganic salts with methyl ethyl ketone (4 L). The filtrate was concentrated on a rotary evaporator while increasing the temperature to 90° C. under house vacuum. After the condensation had stopped, the oil was held at 90° C. under vacuum for an additional two hours to ensure the remaining 1,3-dibrompropane below 8% by GC analysis. The residue was dissolved in 3 L of methyl alcohol, and the white slurry was cooled slowly to about 0–5° C. and held at that temperature overnight. The product was filtered, washed with cold methyl alcohol (6 L), and dried at 30° C. for about 20 hours to afford about 1234 g of compound (a) in 84% yield (99.4% pure by GC). 1H-NMR (CDCl3): 7.3(2H, m), 7.1(2H, m), 7.0(2H, m), 6.9(2H, m), 4.1(2H, m); 3.6(2H, m); 2.3(2H, m).

Workup

  1. temperatureThe off-white slurry was heated to
  2. temperaturea gentle reflux (˜83° C.)
  3. waitheld at that temperature for 16 hours
  4. temperatureThe off white slurry was cooled to 25° C.
  5. filtrationvacuum filtered
  6. washwashing the cake of inorganic salts with methyl ethyl ketone (4 L)
  7. concentrationThe filtrate was concentrated on a rotary evaporator
  8. temperaturewhile increasing the temperature to 90° C. under house vacuum
  9. waitthe oil was held at 90° C. under vacuum for an additional two hours
  10. dissolutionThe residue was dissolved in 3 L of methyl alcohol
  11. temperaturethe white slurry was cooled slowly to about 0–5° C.
  12. customheld at that temperature overnight
  13. filtrationThe product was filtered
  14. washwashed with cold methyl alcohol (6 L)
  15. customdried at 30° C. for about 20 hours

Sources & evidence

ORD record
ord-38f30425170944258209a7f0638b0835
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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