Allyl bromide → Methyl 3-(4-((3-(allyloxy)phenyl)ethynyl)phenyl)propanoate

HRID 2043023Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:23][CH:24]=[CH2:25]>>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1)[CH:24]=[CH2:23]

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 58319096Methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate

Product 1

HCID 58319102Methyl 3-(4-((3-(allyloxy)phenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate (100 mg, 0.45 mmol) and 3-bromoprop-1-ene (133 mg, 0.96 mmol) according to the general procedure IV to give 101 mg (70%) of a pale yellow oily product. Rf=0.55 (EtOAc:PE, 1:1); 1H NMR (CDCl3): δ 7.45 (d, J=8.0 Hz, 2H), 7.24 (t, J=1.3 Hz, 1H), 7.18 (d, J=8.0 Hz, 2H), 7.12 (d, J=7.8 Hz, 1H), 7.06 (t, J=1.9 Hz, 1H) 6.90 (dd, J=8.3 Hz, 2.5 Hz, 1H), 6.10-6.00 (m, 1H), 5.42 (dd, J=17.3 Hz, 1.5 Hz, 1H), 5.30 (dd, J=10.5 Hz, 1.3 Hz, 1H), 4.55 (dt, J=5.3 Hz, 1.3 Hz, 2H), 3.67 (s, 3H), 2.96 (t, J=7.8 Hz, 2H), 2.63 (t, J=7.8 Hz, 2H); 13C NMR (CDCl3): δ 173.1, 158.3, 140.9, 133.0, 131.7, 129.4, 128.3, 124.3, 124.3, 121.1, 117.7, 117.2, 115.6, 89.1, 89.0, 68.8, 51.6, 35.4, 30.8; MALDI-MS m/z 343.4 (M+Na+).

Sources & evidence

ORD record: ord-52f36fbce38c4aec91edd095e7731e4e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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