Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate → (4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-nitro-1,1'-biphenyl-4-yl)acetic acid

HRID 2076647Notes

Reaction equation

HRID 2076647 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]C)=[O:16])=[CH:10][C:9]=2[N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.Br[CH2:23][C:24]1[C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:28]([O:37]C(OC(C)(C)C)=O)[C:27]([C:45]([F:48])([F:47])[F:46])=[CH:26][CH:25]=1>>[C:33]([O:32][C:30]([C:29]1[C:28]([OH:37])=[C:27]([C:45]([F:46])([F:47])[F:48])[CH:26]=[CH:25][C:24]=1[CH2:23][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

3

Reactant 2

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 86088130Methyl (4'-hydroxy-2-nitro-1,1'-biphenyl-4-yl)acetate

Product 1

HCID 11570241(4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-nitro-1,1'-biphenyl-4-yl)acetic acidYield 7%

Procedure

According to a method similar to Example (40-2), Example (33-5) and Example (17-4), from methyl (4′-hydroxy-2-nitro-1,1′-biphenyl-4-yl)acetate (1.71 g, 3.76 mmol) obtained in Example (37-1) and tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (1.08 g, 3.76 mmol) obtained in Example (28-5), the title compound was obtained as a yellow oil (138 mg, three-step total yield: 7%).

Sources & evidence

ORD record
ord-91b0d7bea2a24cbcabff8bbb3f2d977c
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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