Hydrogen Bromide → 1-Bromo-6-methyl-2,6-heptadien-4-yne

HRID 649012Notes

Reaction equation

HRID 649012 reaction equation
[CH3:1][C:2](=[CH2:9])[C:3]#[C:4][CH:5](O)[CH:6]=[CH2:7].[BrH:10]>>[Br:10][CH2:7][CH:6]=[CH:5][C:4]#[C:3][C:2]([CH3:1])=[CH2:9]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 20144474HCID 20144474, compound

Product 1

HCID 539034891-Bromo-6-methyl-2,6-heptadien-4-yne

Procedure

An alcoholic solution of 6-methyl-1,6-heptadien-4-yn-3-ol is added dropwise to 40 ml of fuming HBr and the mixture stirred for 1.5 hours at room temperature. The reaction mixture is poured onto ice and extracted with hexane. The organic phase is repeatedly washed with aqueous NaCl, dried and concentrated on a rotary evaporator. The oily reaction product consists (according to NMR) of a 3:1 mixture of (E)- and (Z)-1-bromo-6-methyl-2,6-heptadien-4-yne and is directly employed for further reaction.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted with hexane
  3. washThe organic phase is repeatedly washed with aqueous NaCl
  4. customdried
  5. concentrationconcentrated on a rotary evaporator
  6. addition(according to NMR) of a 3:1 mixture of (E)- and (Z)-1-bromo-6-methyl-2,6-heptadien-4-yne
  7. customis directly employed for further reaction

Sources & evidence

ORD record
ord-c4e581f1009f4d19a24968f8f032ff3f
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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