p-Toluenesulfonic acid → HCID 71270780, compound

HRID 2175789Notes

Reaction equation

HRID 2175789 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6](NC(C)(C)C)=[O:7])=[C:4]([CH2:15][CH2:16][OH:17])[C:3]=1[F:18].CC1C=CC(S(O)(=O)=O)=CC=1.C1COCC1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([F:18])=[C:4]2[C:5](=[CH:13][CH:14]=1)[C:6](=[O:7])[O:17][CH2:16][CH2:15]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 71271593HCID 71271593, compound

Product 1

HCID 71270780HCID 71270780, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-N-tert-butyl-3-fluoro-2-(2-hydroxyethyl)benzamide. (1.8 g, 5.7 mmol) and TsOH (1.3 g, 6.9 mmol) in toluene (100 mL)/THF (10 mL) was heated to reflux. After 1 h, TLC and LC/MS analysis indicated complete conversion. The solution was concentrated to dryness followed by dilution with Et2O (150 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated affording the title compound: LC-MS: m/z 246.92 (M+H)+.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19eb6a5fd47341d18e676f640ca3ca4b
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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