Dimethylformamide → 1-Bromo-4-[(2-ethylhexyl)oxy]benzene

HRID 988928Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18]Br)[CH3:16].CN(C=O)C>CCOCC.CCCCCC.O>[CH2:15]([CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:16]

Participants

Conditions

Temperature: 90 °C

Procedure

To a 1-L round-bottomed flask were added 4-bromophenol (60.0 g, 0.35 mol), potassium carbonate (52.7 g, 0.38 mol), 2-ethylhexyl bromide (73.7 g, 0.38 mol) and DMF 200 mL. The reaction mixture was stirred at 90° C. under nitrogen overnight. The reaction was poured into water and extracted with ether three times and the combined organic phase was washed with water three times and dried over MgSO4. After solvent was removed, the crude product was obtained as light brown liquid. Pure product was obtained by column chromatography on silica gel using ether/hexane (10/90) as an eluent to give 71.2 g of light yellow liquid at 72% yield. 1H NMR (CDCl3)δ (ppm): 0.88-0.93 (m, 6 H, CH3), 1.27-1.46 (m, 8 H), 1.65-1.74 (m, 1 H), 3.78 (d, J=5.7 Hz, 2 H, OCH2), 6.76 (d, J=8.9 Hz, 2 H), 7.33 (d, J=8.9 Hz, 2 H). 13C NMR (CDCl3): 11.08, 14.08, 23.03, 23.80, 29.05, 30.46, 39.29, 70.72, 112.42, 116.29, 132.11, 158.47. FD-MS: m/z 285 (M+).

Workup

extractionextracted with ether three times
washthe combined organic phase was washed with water three times
dry with materialdried over MgSO4
customAfter solvent was removed
customthe crude product was obtained as light brown liquid
customPure product was obtained by column chromatography on silica gel
customto give 71.2 g of light yellow liquid at 72% yield

Sources & evidence

ORD record: ord-208a96f7ae5e47ebb09fccb3b3d33a5c
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638644B2

Reaction notes

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