Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate → [5-(4-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}phenyl)-2-thienyl]acetic acid

HRID 2076638Notes

Reaction equation

HRID 2076638 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:7]([O:16]C(OC(C)(C)C)=O)[C:6]([C:24]([F:27])([F:26])[F:25])=[CH:5][CH:4]=1.[OH:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[S:39][C:38]([CH2:40][C:41]([O:43]CC)=[O:42])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1>>[C:12]([O:11][C:9]([C:8]1[C:7]([OH:16])=[C:6]([C:24]([F:27])([F:25])[F:26])[CH:5]=[CH:4][C:3]=1[CH2:2][O:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[S:39][C:38]([CH2:40][C:41]([OH:43])=[O:42])=[CH:37][CH:36]=2)=[CH:33][CH:34]=1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 86088129Ethyl[5-(4-hydroxyphenyl)-2-thienyl]acetate

Product 1

HCID 67119218[5-(4-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}phenyl)-2-thienyl]acetic acidYield 14%

Procedure

According to a method similar to Example (2-3), Example (33-5) and Example (17-4), from tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (366 mg, 0.8 mmol) obtained in Example (28-5) and ethyl [5-(4-hydroxyphenyl)-2-thienyl]acetate (211 mg, 0.8 mmol) obtained in Example (28-6), the title compound was obtained as a colorless powder (56 mg, three-step total yield: 14%).

Sources & evidence

ORD record
ord-6298eb310b134ee585ba84b99b7cef7c
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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