Hydrochloric Acid → HCID 86696899, compound

HRID 1399986Notes

Reaction equation

HRID 1399986 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[OH-].[Na+].[O:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][OH:20].Cl>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:20][CH2:19][CH:15]1[CH2:16][CH2:17][CH2:18][O:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7360Tetrahydrofurfuryl alcoholHCID 14798Sodium HydroxideHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 86696899HCID 86696899, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To an ice cold solution of 2-bromo-1-fluoro-4-nitro-benzene (5.0 g, 22.72 mmol) in DMSO (40 mL) was added NaOH (1.36 g, 34.09 mmol) and (tetrahydrofuran-2-yl)methanol (3.47 g, 34.09 mmol) at 0° C. The mixture was stirred at RT for 1 h, then poured into H2O (50 mL), the pH adjusted ˜7 with 1M HCl and extracted with EtOAc (2×250 mL). The combined organics were washed with H2O, brine, dried (Na2SO4), filtered and concentrated in vacuo to obtain i (6.50 g, 95%). 1HNMR (CDCl3, 400 MHz): δ 8.46 (d, J=2.40 Hz, 1H), 8.20 (dd, J=2.40 and 9.20 Hz respectively, 1H), 6.98 (d, J=9.20 Hz, 1H), 4.36 (m, 1H), 4.16 (m, 2H) 3.97 (m, 1H) 3.86 (m, 1H) 2.07 (m 2H) and 1.95 (m, 2H).

Workup

  1. extractionextracted with EtOAc (2×250 mL)
  2. washThe combined organics were washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto obtain i (6.50 g, 95%)

Sources & evidence

ORD record
ord-d0eb571f2ce94262ba812869904b823f
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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