Phenethyl bromide → HCID 22328605, compound

HRID 586129Notes

Reaction equation

HRID 586129 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Li]CCCC.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:24][CH3:25])=[C:20]([CH:23]=1)[CH:21]=[O:22]>C1COCC1.CCCCCC>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:24][CH3:25])=[C:20]([CH:23]=1)[CH:21]([OH:22])[C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH3:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 906845-Bromo-2-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 22328605HCID 22328605, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred −78° solution of p-bromoethylbenzene (2.03 g, 11 mmol) in 10 mL of dry THF under Ar was added 5 mL of 2.5 M n-BuLi (12 mmol) in hexane over 10 min. The temperature was allowed to rise to −10° over 2 hr whereupon the reaction was cooled to −78° before adding solid 5-bromo-2-methoxybenzaldehyde (2.15 g, 10 mmol). After stirring overnight at 20°, the reaction was quenched with saturated aq. NH4Cl and diluted 5 fold with H2O prior to 3 extractions with EtOAc. The combined EtOAc fractions were washed with brine and dried over Na2SO4. After concentration using a rotary evaporator, the residue was chromatographed on silica gel using 10% EtOAc/hexane to elute 1.44 g of 5-bromo-2-methoxy-4′-ethylbenzhydrol.

Workup

  1. temperaturewas cooled to −78°
  2. customthe reaction was quenched with saturated aq. NH4Cl
  3. additiondiluted 5 fold with H2O
  4. extractionto 3 extractions with EtOAc
  5. washThe combined EtOAc fractions were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customa rotary evaporator
  9. customthe residue was chromatographed on silica gel using 10% EtOAc/hexane
  10. washto elute 1.44 g of 5-bromo-2-methoxy-4′-ethylbenzhydrol

Sources & evidence

ORD record
ord-27d661ec7b0c4603aae42dc2fbb968b0
Source dataset
uspto-grants-2005_08
Patent number
US06936590B2

Reaction notes

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