Phenol → 1-Bromo-4-(2-methyl-1-phenoxypropyl)benzene

HRID 1501052Notes

Reaction equation

C(OC(N=NC(OC(C)C)=O)=O)(C)C.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([OH:26])[CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1.[C:27]1(O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]([CH3:24])[CH3:25])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Azodicarboxylic acid diisopropyl ester (824 mg, 4.1 mmol) was added to the mixture of 1-(4-bromophenyl)-2-methylpropan-1-ol (620 mg, 2.7 mmol), phenol (307 mg, 3.2 mmol), triphenylphosphine (1.07 g, 4.1 mmol) and tetrahydrofuran (15 mL) at 20° C. Then the mixture was stirred at 20° C. for 12 hours. The resultant mixture was washed with water (20 mL×2). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to gave 1-bromo-4-(2-methyl-1-phenoxypropyl)benzene as a colorless oil (353 g, 44%). 1H NMR (300 MHz, CDCl3): δ 8.07-7.98 (m, 2H), 7.56-7.48 (m, 2H), 7.32-7.28 (m, 2H), 6.84-6.77 (m, 3H), 4.49 (d, J=6.6 Hz, 1H), 2.35-2.30 (m, 1H), 1.01 (d, J=6.6 Hz, 6H).

Workup

washThe resultant mixture was washed with water (20 mL×2)
customThe organic phase was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a residue
customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record: ord-7567d829ce31424cadb65a6f5114ac1e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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