1-(Azidomethyl)-2,3-difluoro-5-methoxybenzene → HCID 68283856, compound

HRID 1527455Notes

Reaction equation

HRID 1527455 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([F:13])[C:6]=1[F:14])=[N+]=[N-]>CCO.[Pd]>[F:14][C:6]1[C:7]([F:13])=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[CH2:4][NH2:1]

Participants

4

Reactant 1

HCID 866738621-(Azidomethyl)-2,3-difluoro-5-methoxybenzene

Product 1

HCID 68283856HCID 68283856, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-azidomethyl-2,3-difluoro-5-methoxy-benzene (710 mg, 3.57 mmol) in EtOH (20 mL) was added Pd/C 10% (70 mg) and the reaction mixture was stirred at RT overnight under an H2 atmosphere. The reaction mixture was filtered through Celite, followed by washing with EtOH and CH2Cl2. The combined filtrates were evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (CH2Cl2/acetone 9:1, then CH2Cl2/MeOH 9:1) to afford the title compound as a yellowish oil. TLC Rf (CH2Cl2/MeOH 9:1)=0.32; MS (LC/MS): 174.0 [M+H]+; tR (HPLC conditions c): 2.30 min.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washby washing with EtOH and CH2Cl2
  3. customThe combined filtrates were evaporated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel (CH2Cl2/acetone 9:1

Sources & evidence

ORD record
ord-8b6a2a67c56b48dea4ac062bc95ce0f4
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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