Ethanol → HCID 68283673, compound

HRID 1527458Notes

Reaction equation

HRID 1527458 reaction equation
O=S(Cl)Cl.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[F:15])[C:9]([OH:11])=[O:10].[CH3:19][CH2:20]O>>[CH2:19]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:14]([F:15])=[C:6]([Br:5])[CH:7]=1)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 547587233-Bromo-4-fluoro-5-nitrobenzoic acid

Product 1

HCID 68283673HCID 68283673, compound

Procedure

SOCl2 (33.7 g, 0.283 mol) was added dropwise to a solution of 3-bromo-4-fluoro-5-nitro-benzoic acid (37.4 g, 0.142 mol) in EtOH (300 mL). The reaction mixture was refluxed overnight, cooled to RT and subsequently concentrated under reduced pressure. The residue was dissolved in EtOAc (300 mL), washed twice with water (50 mL), dried (Na2SO4) and concentrated to give the title compound as yellow solid. 1H-NMR (300 MHz, CDCl3): δ (ppm) 8.65 (m, 1H), 8.53 (m, 1H), 4.46 (m, 2H), 1.45 (m, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationsubsequently concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (300 mL)
  4. washwashed twice with water (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1dbcad47e9b04647a6ef904e36dbc31f
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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