HCID 19072467, compound → 1-(4-Bromobutyl)-2-methoxybenzene

HRID 1955883Notes

Reaction equation

HRID 1955883 reaction equation
BrC1C=CC=CC=1OC.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22].[CH3+3](CC)#C>O1CCCC1>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 19072467HCID 19072467, compoundHCID 178461644HCID 178461644, compound

Product 1

HCID 190724681-(4-Bromobutyl)-2-methoxybenzeneYield 922.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-bromobutyl)anisole 2-Bromoanisole (2.0 g, 1.07 mmol) in tetrahydrofuran (20 ml) was cooled to -78° C. under nitrogen and secondary butyrithium (1.3 M, 10 ml, 1.3 eq) was charged into the resulting solution for two hours. The solution was quenched with 1,4-dibromobutane (3.2 g) and allowed to stir at ambient temperature overnight. The nmixture was diluted with ethyl acetate, washed with water and brine, and concentrated to an oil. Following chromatography on a SiO2 column, 2.4 g of 2-(4-bromobutyl)anisole were obtained.

Workup

  1. customThe solution was quenched with 1,4-dibromobutane (3.2 g)
  2. additionThe nmixture was diluted with ethyl acetate
  3. washwashed with water and brine
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-a2505edf11454669b7946498a51eaa9c
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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