3-Bromo-1-propanol → 3-[3-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester

HRID 459347Notes

Reaction equation

HRID 459347 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[CH3:6][O:7][C:8](=[O:20])[CH:9]([O:18][CH3:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](O)[CH:12]=1.C(OC(=O)[C@@H](OC)CC1C=CC(OCCCBr)=CC=1)C>>[CH3:6][O:7][C:8](=[O:20])[CH:9]([O:18][CH3:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:5][CH2:4][CH2:3][CH2:2][Br:1])[CH:12]=1

Participants

4

Reactant 3

HCID 123083-Bromo-1-propanolHCID 588228023-(3-Hydroxy-phenyl)-2-methoxy-propionic acid methyl esterHCID 58822859(2S)-3-[4-(3-Bromopropoxy)-phenyl]-2-methoxy-propionic acid ethyl ester

Product 1

HCID 588228613-[3-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester

Procedure

The title compound was prepared from 3-bromo-propan-1-ol (Example 284, Step 1) and 3-(3-hydroxy-phenyl)-2-methoxy-propionic acid methyl ester (Example 291, Step 4) via the same procedure used for the preparation of (2S)-3-[4-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 284, Step 2). 1H-NMR (CDCl3, 200.15 MHz): 7.26–7.16 (m, 1H), 6.80 (t, 3H, J=7.3), 4.09 (t, 2H, J=5.9), 3.97 (dd, 1H, J=7.3, 5.4), 3.73 (s, 3H), 3.60 (t, 2H, J=6.4), 3.36 (s, 3H), 3.00 (s, 1H), 2.97 (d, 1H, J=3.2), 2.31 (qn, 2H, J=6.2).

Sources & evidence

ORD record
ord-6610760409314ff89cc82b1a63e5601b
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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