N-bromobutanimide → 1-Bromo-4-methoxy-5-(3-methoxy-propoxy)-2-methyl-benzene

HRID 1158456Notes

Reaction equation

HRID 1158456 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].[Br:16]N1C(=O)CCC1=O>CC#N>[Br:16][C:6]1[CH:5]=[C:4]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH3:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 577907582-Methoxy-1-(3-methoxy-propoxy)4-methyl-benzene

Product 1

HCID 592239541-Bromo-4-methoxy-5-(3-methoxy-propoxy)-2-methyl-benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-methoxy-1-(3-methoxy-propoxy)-4-methyl-benzene (2.00 g, 9.51 mmol) in MeCN (30 mL) is added N-bromosuccinimide (1.96 g, 10.5 mmol) at room temperature. Stirring is continued for 2 hrs, followed by evaporation of the solvent. The title compound is obtained after flash chromatography on silica gel (hexane/AcOEt 6:1) as an oil. MS: 289.0/291.0 [M]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 5.04 min. 1H-NMR (CDCl3): δ 2.13 (m, 2H), 2.36 (s, 3H), 3.39 (s, 3H), 3.58 (m, 2H), 3.87 (s, 3H), 4.12 (m, 2H), 6.77 (s,1H), 7.08 (s, 1H) ppm.

Workup

  1. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-61fd5f747cda4ceb8476ce3e741b326a
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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