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

HRID 237286Notes

Reaction equation

HRID 237286 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]>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

4

Reactant 2

HCID 6385Tert-ButylamineHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 67343773(4-Bromo-2-fluoro-benzylidene)-tert-butyl-amineYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromo-2-fluorobenzaldehyde (10 g, 47 mmol), tert-butyl amine (6.1 mL, 57 mmol) and 4 Å powder molecular sieves (8.0 g) in 160 mL CH2Cl2 (160 mL) was stirred at rt for 18 h. The reaction mixture was filtered through a pad of celite and concentrated to give the title compound (9.9 g, 78%). MS (ESI): mass calcd. for C11H13BrFNO, 258.1; m/z found, 260.0 [M+H]+. 1H NMR (CDCl3): 10.32 (s, 1H), 8.48 (s, 1H), 7.89 (t, J=8.1 Hz, 1H), 7.50-7.20 (m, 1H), 1.49-1.08 (m, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4c41c98507e04e50a3fc428172c4cd5e
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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