2-Nitro-4-(trifluoromethyl)phenol → HCID 59520419, compound

HRID 1162514Notes

Reaction equation

HRID 1162514 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].[CH2:15](OS(C)(=O)=O)[C:16]#[C:17][CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH2:15]([O:14][C:5]1[CH:6]=[CH:7][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:16]#[C:17][CH3:18]

Participants

5

Reactant 3

HCID 98162-Nitro-4-(trifluoromethyl)phenolHCID 10796Cesium carbonateHCID 11051825HCID 11051825, compound

Product 1

HCID 59520419HCID 59520419, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

2-nitro-4-trifluoromethyl-phenol 7 (4.1 g, 20 mmol) and methanesulfonic acid but-2-ynyl ester 20 (3.0 g, 20 mmol) are dissolved in MeCN. Cs2CO3 is added (13.0 g, 40 mmol) and the mixture is stirred at 90° C. for 12 hours. The mixture is then filtered, concentrated in vacuo, diluted with H2O and extracted three times with DCM. The organic layers are combined, dried (MgSO4), filtered, and concentrated and the remainder purified by column chromatography using a hexanes/EtOAc gradient to afford 1-but-2-ynyloxy-2-nitro-4-trifluoromethyl-benzene 21 as a yellow solid: 1H-NMR (400 MHz, CDCl3) δ=8.06 (d, J=1.7 Hz, 1H), 7.73 (dd, J=8.8 Hz, J=1.8 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 4.81 (q, J=2.3 Hz, 2H), 1.79 (t, J=2.3 Hz, 3H). MS calculated for C11H9F3NO3 (M+H+) 260.1, found 260.3.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationconcentrated in vacuo
  3. additiondiluted with H2O
  4. extractionextracted three times with DCM
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe remainder purified by column chromatography

Sources & evidence

ORD record
ord-d1b88a6cd57d43dbad13fa39d3231f90
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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