4-Fluorobenzonitrile → HCID 21880817, compound

HRID 724465Notes

Reaction equation

[O:1]1[CH2:15][CH:2]1[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH:11]2[O:13][CH2:12]2)[C:5]=1[OH:14].[OH-].[Na+].F[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>CC(N(C)C)=O.C(OCC)(=O)C>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([O:14][C:5]2[C:4]([CH2:3][CH:2]3[O:1][CH2:15]3)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:10][CH:11]2[O:13][CH2:12]2)=[CH:20][CH:21]=1)#[N:24]

Participants

Conditions

Temperature: 50 °C

Procedure

2,6-Diallylphenol (3.8 gm, 0.02 mol) was oxidized with m-chloroperbenzoic acid as described in Example 1 to give 2,6-di(2,3-epoxypropyl)phenol. MS m/z 206 (M+ calcd for C12H14O3=206). H NMR (300 MHz, CDCl3) d 2.65 (d, 2, CH2 epoxypropyl) 2.75–2.96 (CH2 epoxypropyl), 3.12 (d, 2, CH epoxypropyl), 3.25–3.35(m, 2, CH epoxypropyl), 6.80 (t, 1, aromatic), 7.10 (d, 2, aromatic). The product 2,6-di(2,3-epoxypropyl)phenol was diluted with dimethylacetamide (50 ml) and neutralized with sodium hydroxide. 4-Fluorobenzonitrile (1 equivalent of the phenol) was added and the mixture heated and stirred overnight at 50° C. After cooling, the reaction was diluted with ethyl acetate and washed with water (4×), dried over MgSO4 and evaporated to give 2,6-di(2,3epoxypropyl)phenyl 4-cyanophenyl ether. MS m/z 307 (M+ calcd for C19H17O3N=307). H NMR (300 MHz, CDCl3) d 2.50, (d, 2, CH2 epoxypropyl CH2), 2.65–2.90 (m, 4, CH2 epoxypropyl), 3.15–3.30 (m, 2, CH2 epoxypropyl), 3.45–3.75 (m, 2, epoxypropyl CH), 6.75–7.06 (m, 3, aromatic), 7.00–7.75 (m, 4, aromatic).

Workup

temperaturethe mixture heated
temperatureAfter cooling
washwashed with water (4×)
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-5c179b9060ca4e8fae0a3b3d0fb4e837
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141684B2

Reaction notes

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