Hydrochloric Acid → 1-(4-Bromophenyl)-2-methylbutan-1-ol

HRID 911656Notes

Reaction equation

HRID 911656 reaction equation
Br[CH:2]([CH2:4][CH3:5])[CH3:3].[Mg].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.Cl>C1COCC1.O>[OH:13][CH:12]([C:11]1[CH:14]=[CH:15][C:8]([Br:7])=[CH:9][CH:10]=1)[CH:2]([CH3:3])[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 65542-BromobutaneHCID 707414-BromobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 108477881-(4-Bromophenyl)-2-methylbutan-1-olYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add slowly a solution of 2-bromo-butane (4.8 g, 35 mmol) in anhydrous THF (20 mL) to a stirring mixture of magnesium (980 mg, 37 mmol) and anhydrous THF (10 mL) under a nitrogen atmosphere. Heat the mixture at reflux for 30 min. Cool the mixture to room temperature and add 4-bromo-benzaldehyde (5.36 g, 29 mmol). After stirring for 5 min, cool the mixture in an ice-bath and acidify with 3N aqueous HCl (50 mL). Dilute the mixture with water and extract twice with diethyl ether. Wash the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 20:1 and 1:1) to provide the desired intermediate as a clear oil (2 g, 28%). MS (APCI) m/z: 243 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 30 min
  3. temperaturecool the mixture in an ice-bath
  4. extractionextract twice with diethyl ether
  5. washWash the combined organic extracts with water and brine
  6. dry with materialDry the organic phase over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 20:1 and 1:1)

Sources & evidence

ORD record
ord-11c1268911ee4315b26fb3e9acccced4
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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