Trifluoroacetic acid → 5-Chloro-4-((7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)-2-fluorobenzoic acid

HRID 1427912Notes

Reaction equation

HRID 1427912 reaction equation
[Cl:1][C:2]1[C:3]([CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:25]3[CH2:24][CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21][C:20]=3[CH:19]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:25]3[CH2:24][CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21][C:20]=3[CH:19]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86702927Tert-butyl 5-chloro-4-((7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)-2-fluorobenzoate

Product 1

HCID 867029305-Chloro-4-((7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-chloro-4-((7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)-2-fluorobenzoate (220 mg, 0.53 mmol) in DCM (5 mL) was added trifluoroactic acid (5 mL). After stirred at room temperature for 3 h, the reaction mixture was concentrated under reduced pressure and the residue was used in next step without further purification (0.22 g, crude). LCMS (ESI) m/z: 361.0 [M−H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was used in next step without further purification (0.22 g, crude)

Sources & evidence

ORD record
ord-a3f910b2a3bc42c0b5f31d74ebc0fb89
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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