Allyl bromide → 4-(4-Prop-2-enoxyphenyl)benzonitrile

HRID 257292Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:16][C:17](C)([O-])[CH3:18].[K+].C(Br)C=C>C1COCC1>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH:17]=[CH2:16]

Participants

Conditions

Temperature: 25 °C

Procedure

The crude phenol 2i [4-(4-hydroxyphenyl)-benzonitrile] was dissolved in 250 mL of anh THF and added to a 500-mL 3-neck round-bottom flask and stirred at 25° C. Potassium tert-butoxide (0. 89 g, 8 mmol) was added to the solution, which turned yellow. Allyl bromide was added in excess (5.0 mL, 40 mmol) and the mixture was refluxed overnight. The THF and allyl bromide were removed by rotoevaporation. The resultant sludge was extracted 5 times with mL of hexane. This material was purified chromatographically (200 mesh Kieselgel 60, 2 % EtOAc 98% in hexane) to afford 1.0 g of white crystalline material (65%): mp 68°-69° C.; IR 3083, 3013, 2884, 2225, 1604, 1492, 1455, 1291, 1249, 1180, 995, 940, 824, 533 cm-1 ; 1H NMR δδ 7.6-7.8 (m, 4H), 7.4-7.5 (d, 2H), 6.9-7.0 (d, 2 H), 5.9-6.0 (m, 1 H), 5.2-5.4 (m, 2 H), 4.5 (d, 2 H); MS m/e 235 (M+), 220, 207, 166. Anal. Calcd for C14H11NO: C, 81.68; H, 5.56. Found C, 81.56; H, 5.68.

Workup

additionadded to a 500-mL 3-neck round-bottom flask
temperaturethe mixture was refluxed overnight
customThe THF and allyl bromide were removed by rotoevaporation
extractionThe resultant sludge was extracted 5 times with mL of hexane
customThis material was purified chromatographically (200 mesh Kieselgel 60, 2 % EtOAc 98% in hexane)

Sources & evidence

ORD record: ord-e4c95858e44041f18a091f5419dbe2c5
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262052

Reaction notes

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