2-(Bromomethyl)-1-fluoro-3-nitrobenzene → 1-Fluoro-2-[(methylsulfanyl)methyl]-3-nitrobenzene

HRID 561367Notes

Reaction equation

HRID 561367 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:4]Br.[CH3:13][S-:14].[Na+]>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:4][S:14][CH3:13]

Participants

4

Reactant 2

HCID 747792-(Bromomethyl)-1-fluoro-3-nitrobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 583923371-Fluoro-2-[(methylsulfanyl)methyl]-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16.36 g (69.9 mmol) of 2-fluoro-6-nitrobenzyl bromide were introduced into 410 ml of THF, 5.88 g (83.9 mmol) of sodium methanethiolate were added in portions, and the mixture was stirred at RT for 24 h. The solid was filtered off and the filtrate was freed of solvent in a rotary evaporator. The residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10/1) to result in 11.43 g (81% of theory) of the title compound.

Workup

  1. additionwere added in portions
  2. filtrationThe solid was filtered off
  3. customthe filtrate was freed of solvent in a rotary evaporator
  4. customThe residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10/1)

Sources & evidence

ORD record
ord-3a5ef9bd498044e6899cf041b242a62c
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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