Trifluoroacetic acid → HCID 86703663, compound

HRID 1849779Notes

Reaction equation

HRID 1849779 reaction equation
[Cl:1][C:2]1[C:3]([CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]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>ClCCl>[Cl:1][C:2]1[C:3]([CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]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 86703662HCID 86703662, compound

Product 1

HCID 86703663HCID 86703663, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-chloro-4-(cyclohexyloxymethyl)-2-fluorobenzoate (1.86 g, 5.43 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid (20 mL). The reaction solution was stirred at ambient temperature for 3 hours, then concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 mL), washed with brine (3×25 mL), dried over anhydrous sodium sulfate, filtered the solid. The filtrate was concentrated in vacuo to dryness to afford the title compound (0.50 g, 32% crude yield) which was subjected to next step without any further purification: MS (ES+) m/z 287.0, 285.0 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate (50 mL)
  3. washwashed with brine (3×25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered the solid
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-c1349c60e4784da7b7395d96df6e3fac
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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