Benzyl Bromide → Methyl 3-(4-((3-(benzyloxy)phenyl)ethynyl)phenyl)propanoate

HRID 2043021Notes

Reaction equation

HRID 2043021 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][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([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)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 58319096Methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate

Product 1

HCID 58319103Methyl 3-(4-((3-(benzyloxy)phenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate (98 mg, 0.45 mmol) and (bromomethyl)benzene (142 mg, 1.03 mmol) according to the general procedure IV to give 112 mg (68%) of a pure pale yellow solid. Rf=0.60 (EtOAc:PE, 1:1); 1H NMR (CDCl3): δ 7.46-7.32 (m, 7H), 7.46-7.22 (m, 1H), 7.17 (d, J=8.5 Hz, 2H), 7.14-7.12 (m, 2H), 6.95 (ddd, J=8.3 Hz, 2.8 Hz, 1.0 Hz, 1H), 5.07 (s, 2H), 3.66 (s, 3H), 2.95 (t, J=7.8 Hz, 2H), 2.63 (t, J=7.8 Hz, 2H); 13C NMR (CDCl3): δ 173.8, 158.6, 140.9, 136.7, 131.8, 129.4, 128.6, 128.3, 128.0, 127.5, 124.4, 124.4, 121.1, 117.3, 115.6, 89.2, 89.0, 70.0, 51.6, 35.4, 30.8; MALDI-MS m/z 393.4 (M+Na+).

Sources & evidence

ORD record
ord-f865053964314ec8944d87485e00cd53
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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