2-Bromobutyrate → [2-Chloro-4-(3-cyclopentyl-3-oxo-propyl)-phenoxy]-acetic acid methyl ester

HRID 1453031Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].BrC1C=[CH:23][C:22]([OH:25])=C(F)C=1.BrC(CC)[C:29]([O-])=[O:30]>>[CH3:29][O:30][C:22](=[O:25])[CH2:23][O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:3][C:2]=1[Cl:1]

Participants

Reactant 3

HCID 1523172-Bromobutyrate

HCID 27249814-Bromo-2-fluorophenol

HCID 587626963-(3-Chloro-4-hydroxyphenyl)-1-cyclopentylpropan-1-one

Product 1

HCID 58762565[2-Chloro-4-(3-cyclopentyl-3-oxo-propyl)-phenoxy]-acetic acid methyl esterYield 78%

Procedure

The title compound was prepared analogously to Step 1 from Example A(52), where 3-(3-Chloro-4-hydroxy-phenyl)-1-cyclopentyl-propan-1-one was substituted for 4-Bromo-2-fluorophenol and methyl bromo acetate was substituted for methyl □-bromobutyrate in Step 1 of that example. Yield 78%. 1H NMR (CDCl3) δ: 1.55-1.77 (m, 9H), 2.70-2.85 (m, 4H), 3.80 (s, 3H),), 4.68 (sm 2H), 6.75 (d, J=8.5, 1H), 7.0 (dd, J=8.5, 2.2, 1H), 7.21 (d, J=2.2, 1H).

Sources & evidence

ORD record: ord-788bd369653347a692543d23ce3b8fc8
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473790B2

Reaction notes

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