Methyl 3-(4-Hydroxy-2-methylphenyl)propanoate → 3-[4-(3-Bromo-5-ethyl-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester

HRID 1822317Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.[CH3:11][O:12][C:13](=[O:24])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[CH3:23]>>[CH3:11][O:12][C:13](=[O:24])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=2)=[CH:18][C:17]=1[CH3:23]

Participants

Reactant 2

HCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoate

HCID 187118073,5-Dibromoethylbenzene

Product 1

HCID 578941463-[4-(3-Bromo-5-ethyl-phenoxy)-2-methyl-phenyl]-propionic acid methyl esterYield 56%

Procedure

Compound of 1,3-dibromo-5-ethyl-benzene is reacted with 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester as in Example 18 to afford 0.898 g (56%) of the title compound. Rf=0.32 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C19H21O3Br 376, found 377 and 379 (M+1 and M+3, 100%).

Sources & evidence

ORD record: ord-a04c183c065641e1894daba96423362a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608639B2

Reaction notes

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