2-Bromophenol → HCID 22752746, compound

HRID 1076674Notes

Reaction equation

HRID 1076674 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].Br[CH2:11][CH:12]([Cl:14])[CH3:13]>C(O)C>[Cl:14][CH:12]([CH3:13])[CH2:11][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[Br:2]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 181761-Bromo-2-chloropropaneHCID 5360545Sodium

Product 1

HCID 22752746HCID 22752746, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 23.0 g of sodium metal in 500 ml of absolute ethanol is added in about 0.5 hour a solution of 173.0 g of o-bromophenol in 250 ml of absolute ethanol. The mixture is stirred and heated under reflux for about 0.5 hour, cooled to 0°, and treated, dropwise, with 157.5 g of 1-bromo-2-chloropropane. The last addition requires about 1 hour. The mixture is stirred at 0° for about 2 hours and slowly warmed to reflux during about 2 hours, heated under reflux for about 2 hours, filtered from the precipitated sodium bromide, and the filtrate is concentrated in vacuo at 40° to give about 240.2 g of o-bromophenyl 2-chloropropyl ether as a mobile, colorless liquid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for about 0.5 hour
  3. temperaturecooled to 0°
  4. additiontreated
  5. additionThe last addition
  6. stirringThe mixture is stirred at 0° for about 2 hours
  7. temperatureslowly warmed
  8. temperatureto reflux during about 2 hours
  9. temperatureheated
  10. temperatureunder reflux for about 2 hours
  11. filtrationfiltered from the precipitated sodium bromide
  12. concentrationthe filtrate is concentrated in vacuo at 40°

Sources & evidence

ORD record
ord-7a9e6f7ee532412f91f99918fe489506
Source dataset
uspto-grants-1976_05
Patent number
US03957806

Reaction notes

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