Hydrochloric Acid → 1-(2-Bromophenyl)-1-propanol

HRID 2297733Notes

Reaction equation

HRID 2297733 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].Cl>O1CCCC1>[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]([OH:9])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811292-BromobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 134442791-(2-Bromophenyl)-1-propanolYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (1 mol/L, 60 mL) of ethylmagnesium bromide in tetrahydrofuran was added to a solution (200 mL) of 2-bromobenzaldehyde (5.55 g, 3.0 mmol) in tetrahydrofuran under ice-cooling, followed by stirring for 1 hour while gradually heating the mixture to room temperature. Next, the reaction solution was poured into ice water, and this mixture was neutralized with hydrochloric acid (1 mol/L) and then extracted with ethyl acetate. After the extract was washed with a saturated brine and then dried over sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developed with ethyl acetate/hexane=1/4) to give 1-(2-bromophenyl)-1-propanol (4.5 g, yield 70%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washAfter the extract was washed with a saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (developed with ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-b1f7a7efcae54814bdf28f862372d294
Source dataset
uspto-grants-2002_12
Patent number
US06492392B1

Reaction notes

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