N-bromobutanimide → 3-Bromomethyl-2-fluoro-5-nitro-pyridine

HRID 426265Notes

Reaction equation

HRID 426265 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)Cl>[Br:19][CH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 124081842-Fluoro-3-methyl-5-nitropyridine

Product 1

HCID 596868623-Bromomethyl-2-fluoro-5-nitro-pyridineYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-3-methyl-5-nitro-pyridine (445 mg, 2.85 mmol) was dissolved in 20 mL DCM. NBS (1.01 g, 5.7 mmol, 2 eq.) was added. The reaction was stirred at room temperature for 2 days. HPLC showed 20% conversion. The reaction was concentrated down and purified (silica gel, 0-80% EtOAc/hexane) to give light yellow oil (100 mg, 15%). 1H NMR (300 MHz, CD3OD): δ 8.39 (m, 2H), 7.61 (m, 1H), 4.86 (s, 2H).

Workup

  1. concentrationThe reaction was concentrated down
  2. custompurified (silica gel, 0-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-f890b33df34d4a4f84e7f3ebe2e89595
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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