Hydrochloric Acid → (2-Bromo-2-propen-1-yl)benzene

HRID 543466Notes

Reaction equation

HRID 543466 reaction equation
[Br:1][C:2]([CH2:4]Br)=[CH2:3].[C:6]1([Mg]Br)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Mg].BrC1C=CC=CC=1.Cl>CC(C)=O.C(=O)=O.O.CCOCC>[Br:1][C:2]([CH2:4][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 105522,3-DibromopropeneHCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 2757160(2-Bromo-2-propen-1-yl)benzene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 18522661Acetone cardiceSolvent2×

Procedure

A 1000 ml 3-necked round-bottomed flask was fitted with a mechanical stirrer through a mineral oil sealed bearing, a reflux condenser and 1000 ml addition funnel. A mixture of 156 g of 2,3-dibromopropene and 150 ml of dry ethyl ether was added. The flask was cooled to 0° C. in acetone/dry-ice and a solution of phenyl magnesium bromide, prepared from 18.7 g of magnesium, 120.8 g of bromobenzene, and 350 ml of dry ether was added at such a rate so that the temperature did not exceed 15° C. The addition took about one hour. Stirring was continued and the acetone/dry-ice bath was replaced with a heating mantle. The mixture was gently refluxed for 2 hours, after which time the flask was again cooled and a solution of 15 ml 36% hydrochloric acid and 150 ml water was added dropwise by means of an addition funnel. The contents of the flask were then transferred to a separatory funnel, and the ether layer was separated and dried over anhydrous sodium sulfate.

Workup

  1. customA 1000 ml 3-necked round-bottomed flask was fitted with a mechanical stirrer through a mineral oil
  2. customsealed
  3. additiona reflux condenser and 1000 ml addition funnel
  4. additionwas added
  5. additionwas added at such a rate so that the temperature
  6. customdid not exceed 15° C
  7. additionThe addition
  8. temperatureThe mixture was gently refluxed for 2 hours
  9. temperatureafter which time the flask was again cooled
  10. customThe contents of the flask were then transferred to a separatory funnel
  11. customthe ether layer was separated
  12. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-e7a425109a1d4aefb7bf47c17e55cd86
Source dataset
uspto-grants-1984_05
Patent number
US04446076

Reaction notes

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