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

HRID 2076625Notes

Reaction equation

HRID 2076625 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11]C)=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.Br[CH2:21][C:22]1[C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[C:26]([O:35]C(OC(C)(C)C)=O)[C:25]([C:43]([F:46])([F:45])[F:44])=[CH:24][CH:23]=1>>[C:31]([O:30][C:28]([C:27]1[C:26]([OH:35])=[C:25]([C:43]([F:44])([F:45])[F:46])[CH:24]=[CH:23][C:22]=1[CH2:21][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:3]2[CH:4]=[CH:5][C:6]([CH2:8][C:9]([OH:11])=[O:10])=[CH:7][C:2]=2[Cl:1])=[CH:14][CH:15]=1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 86088067Methyl (2-chloro-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

Product 1

HCID 11706504(4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-chloro-1,1'-biphenyl-4-yl)acetic acidYield 15%

Procedure

According to a method similar to Example (2-3), Example (33-5) and Example (17-4), from methyl (2-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetate (150 mg, 0.54 mmol) obtained in Example (23-3) and tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (455 mg, 1.0 mmol) obtained in Example (28-5), the title compound was obtained as a colorless compound (46 mg, three-step total yield: 15%).

Sources & evidence

ORD record
ord-d600c7bda5054d119c9093303c3d352c
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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