Tert-Butylamine → (4-Bromo-2-fluoro-benzylidene)-tert-butyl-amine

HRID 237245Notes

Reaction equation

HRID 237245 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 67343773(4-Bromo-2-fluoro-benzylidene)-tert-butyl-amineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (900 mL) solution of 4-bromo-2-fluoro-benzaldehyde (50.0 g, 246 mmol) was added tert-butylamine (42.3 mL, 29.3 g, 400 mmol) and MgSO4 (60.0 g, 499 mmol). After 48 h, the solution was filtered and concentrated to give 62.0 g (98%) of the title compound as a yellow liquid. 1H NMR (CDCl3): 8.48 (s, 1H), 7.89 (t, J=8.1 Hz, 1H), 7.32-7.25 (m, 2H), 1.29 (s, 9H).

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d7f966b74b9e4f4c98c34c5c2d9b7444
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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