4-Bromoaniline, N-BOC protected → Benzenamine, 4-bromo-N-methyl-

HRID 57635Notes

Reaction equation

HRID 57635 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)OC(C)(C)C)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27736084-Bromoaniline, N-BOC protectedHCID 21226445Aluminium lithium hydride

Product 1

HCID 2757052Benzenamine, 4-bromo-N-methyl-Yield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Tert-butyl 4-bromophenylcarbamate (5.5 g, 20.21 mmol) was dissolved in THF, Lithium aluminum hydride (2.301 g, 60.63 mmol) was added and it was stirred at 60° C. overnight. Then it was quenched by EA, followed by H2O, concentrated and CH2Cl2 and 1M NaOH was added in, washed with CH2Cl2, extracted with CH2Cl2, dried over Na2SO4, concentrated, purified by flash chromatography (PE: EA=40:3) to give 2.1 g yellow oil.

Workup

  1. customThen it was quenched by EA
  2. concentrationconcentrated
  3. additionCH2Cl2 and 1M NaOH was added in,
  4. washwashed with CH2Cl2
  5. extractionextracted with CH2Cl2
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (PE: EA=40:3)

Sources & evidence

ORD record
ord-1a98748a24e242b1a8f1df327b5aa963
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

Loading…