N-bromobutanimide → 1-Bromo-4-methoxy-2,5-dipropylbenzene

HRID 1816401Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[CH2:12][CH2:13][CH3:14].[Br:15]N1C(=O)CCC1=O>C(#N)C.[Cl-].[Na+].O>[Br:15][C:6]1[CH:5]=[C:4]([CH2:12][CH2:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-methoxy-1,4-dipropylbenzene (2.0 g, 10.4 mmol) in acetonitrile (30 mL) at room temperature was added N-bromosuccinimide (1.85 g, 10.4 mmol) in three portions. The solution was stirred at 60° C. for 20 hr and then most of the solvent was removed in vacuo. Extracton in hexanes (2×100 mL) with 50% saturated brine (75 mL) and flash chromatography with silica gel (100% hexanes) provided the title compound as a colorless liquid (2.50 g, 89% yield): 1H NMR (300 MHz, CDCl3) δ 0.93 (t, 3H, J=7.5 Hz), 0.99 (t, 3H, J=7.6 Hz), 1.60 (m, 4H), 2.50 (t, 2H, J=7.7 Hz), 2.65 (t, 2H, J=7.8 Hz), 3.79 (s, 3H), 6.67 (s, 1H), 7.24 (s, 1H).

Workup

custommost of the solvent was removed in vacuo

Sources & evidence

ORD record: ord-9252d3798cc84aa1bd529c1f11638855
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884814B2

Reaction notes

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