Benzyl Alcohol → HCID 17985978, compound

HRID 1521689Notes

Reaction equation

HRID 1521689 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:11]([OH:13])=[O:12].CN(C=O)C.[CH2:25](O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.N1C=CC=CC=1>[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:11]([O:13][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:12]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 17985978HCID 17985978, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.60 mL), 53.6 mmol) is added to a stirred suspension of 3-fluoro-4-nitrobenzoic acid (5.11 g, 26.8 mmol) in CH2Cl2 (100 mL). DMF (0.1 mL) is added, and the solution stirred for 2 h at room temperature. The solvent is evaporated, and the residue is dissolved in CH2Cl2 (100 mL). Benzyl alcohol (5.54 mL, 53.6 mmol) and pyridine (2 mL) are added and the solution stirred for 16 h. The solvent is removed and the residue purified by filtration through a pad of silica gel, eluting with EtOAc/heptanes (1:9) to afford the title compound (6.8 g, 24.7 mmol).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in CH2Cl2 (100 mL)
  3. stirringthe solution stirred for 16 h
  4. customThe solvent is removed
  5. filtrationthe residue purified by filtration through a pad of silica gel
  6. washeluting with EtOAc/heptanes (1:9)

Sources & evidence

ORD record
ord-8ccd643930214d6389d009d57a441640
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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