Hydrochloric Acid → Benzenamine, 4-bromo-N-methyl-

HRID 1784420

Reaction equation

HRID 1784420 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=O)=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.Cl.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 17474Formamide, N-(4-bromophenyl)-

Product 1

HCID 2757052Benzenamine, 4-bromo-N-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(4-Bromo-phenyl)-formamide D32a (8.2 g, 41 mmol) in dry THF (100 mL) was added BF3.Et2O (8.2 mL, 61 mmol). The mixture was heated to reflux and BH3. THF (103 mL, 103 mmol) added dropwise, the mixture was heated for a further 2 hours. After cooling to room temperature concentrated HCl (100 mL) was added and the mixture stirred for one hour. The pH of the mixture was adjusted to pH 13 using concentrated NaOH. Extraction with ether, drying over MgSO4 and evaporating to dryness gave the subtitled compound as light brown oil (7.58 g). MH+ 186/188. 1H NMR δ (CDCl3) 2.81 (3H, s), 3.63-3.78 (1H, br.s), 6.43-6.52 (2H, d), 7.22-7.30 (2H, d).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturethe mixture was heated for a further 2 hours
  4. additionwas added
  5. extractionExtraction with ether
  6. dry with materialdrying over MgSO4
  7. customevaporating to dryness

Sources & evidence

ORD record
ord-684f4c64fb3a49e28cba37aa5a313993
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Linked notes

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