Toluene → 1-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

HRID 1403805Notes

Reaction equation

[C:1]1(C)C=CC=C[CH:2]=1.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH2:30][C:31]#[N:32])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.BrCCCl>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+].O>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:30]2([C:31]#[N:32])[CH2:2][CH2:1]2)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of (n-C4H9)4NBr (0.50 g, 1.5 mmol), toluene (7 mL) and (3,4-bis-benzyloxy-phenyl)-acetonitrile (14 g, 42 mmol) in NaOH (50 g) and H2O (50 mL) was added BrCH2CH2Cl (30 g, 0.21 mol). The reaction mixture was stirred at 50° C. for 5 h before being cooled to room temperature. Toluene (30 mL) was added and the organic layer was separated and washed with H2O, brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1) to give 1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile (10 g, 66%). 1H NMR (DMSO 300 MHz) δ 7.46-7.30 (m, 10H), 7.03 (d, J=8.4 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 6.89 (dd, J=2.4, 8.4 Hz, 1H), 5.12 (d, J=7.5 Hz, 4H), 1.66-1.62 (m, 2H), 1.42-1.37 (m, 2H).

Workup

temperaturebefore being cooled to room temperature
customthe organic layer was separated
washwashed with H2O, brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated
customThe residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1)

Sources & evidence

ORD record: ord-8c2a14b766bd4343b3fa6b6dd3ffa6c3
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912199B2

Reaction notes

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