1-(Bromomethyl)-2-fluoro-3-nitrobenzene → HCID 59139498, compound

HRID 1046816Notes

Reaction equation

HRID 1046816 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[F:12].[CH3:13][C:14]1[C:15]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:19][C:16]=2[S:17][CH:18]=1>ClCCl.[Cl-].[Zn+2].[Cl-]>[F:12][C:4]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:18]1[S:17][C:16]2[CH:19]=[C:20]([O:23][C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH:21]=[CH:22][C:15]=2[C:14]=1[CH3:13]

Participants

5

Reactant 2

HCID 591391511-(Bromomethyl)-2-fluoro-3-nitrobenzene2×HCID 59139175HCID 59139175, compound

Product 1

HCID 59139498HCID 59139498, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

1-Bromomethyl-2-fluoro-3-nitrobenzene (120 mg, 0.513 mmol) and zinc chloride (71 mg, 0.520 mmol) were added to a solution of 2-(3-methyl-benzo[b]thiophen-6-yloxy)pyrimidine (114 mg, 0.470 mmol) in dichloromethane (1.0 mL), and the mixture was heated under reflux for 17.5 hours. After returning to room temperature, 1-bromomethyl-2-fluoro-3-nitrobenzene (120 mg, 0.513 mmol) and zinc chloride (71 mg, 0.520 mmol) were added thereto, and the mixture was heated under reflux for 23 hours. The reaction mixture was then concentrated under reduced pressure, and purified by column chromatography to yield the title compound (67.5 mg, 36%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17.5 hours
  3. customAfter returning to room temperature
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 23 hours
  6. concentrationThe reaction mixture was then concentrated under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-96b1d566dc3d4fe2bac5a765041259c9
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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