Water → 2-Bromo-3-fluoroaniline

HRID 1908421Notes

Reaction equation

HRID 1908421 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[F:11].[BH4-].[Na+].O>CO.Cl[Ni]Cl>[Br:1][C:2]1[C:3]([F:11])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 183734742-Bromo-1-fluoro-3-nitrobenzene

Product 1

HCID 147700052-Bromo-3-fluoroanilineYield 70%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-1-fluoro-3-nitrobenzene (1.0 g, 5.0 mmol) in CH3OH (50 mL) was added NiCl2 (2.2 g 10 mmol) and NaBH4 (0.50 g 14 mmol) at 0° C. After the addition, the mixture was stirred for 5 min. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL×3). The organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give 2-bromo-3-fluoroaniline (600 mg, 70%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.02 (m, 1H), 6.55-6.49 (m, 1H), 4.22 (br s, 2H).

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with EtOAc (20 mL×3)
  3. dry with materialThe organic layers were dried over anhydrous Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-929fc6bb729c44379869918a46d5b84e
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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