Water → 4-Tert-butyl-3-fluoroaniline

HRID 383407Notes

Reaction equation

HRID 383407 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[F:16])([CH3:6])([CH3:5])[CH3:4].O>CO>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[F:16])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 593949451-Tert-butyl-2-fluoro-4-nitrobenzene

Product 1

HCID 219047584-Tert-butyl-3-fluoroanilineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (289 mg, 7.6 mmol) was added to a solution of 1-tert-butyl-2-fluoro-4-nitrobenzene (750 mg, 3.8 mmol) and NiCl2.6H2O (2.6 g, 11.4 mmol) in MeOH (15 mL) at −15° C. After addition, the mixture was stirred for 2 minutes and water was added to quench the reaction. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated in vacuo to afford 4-tert-butyl-3-fluoroaniline (470 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 7.08-7.02 (m, 1H), 6.42-6.34 (m, 2H), 1.32 (s, 9H). MS (ESI) m/z: 168.2 [M+H]+.

Workup

  1. additionAfter addition
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-72d05fcec54a4d49a91650ea38e0d745
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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