Tetrahydrofuran → 3-Bromo-4-fluoro-α,α-dimethylbenzeneacetaldehyde

HRID 83878Notes

Reaction equation

HRID 83878 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[C:10]#N)[CH:5]=[CH:6][C:7]=1[F:8].CC(C[AlH]CC(C)C)C.C1C[O:26]CC1>>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[CH:10]=[O:26])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 667410412-(3-Bromo-4-fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 866622533-Bromo-4-fluoro-α,α-dimethylbenzeneacetaldehydeYield 92%

Procedure

To a stirred solution of 2-(3-bromo-4-fluorophenyl)-2-methylpropanenitrile (29 g, 120 mmol) in THF (500 mL) at −78° C. was dropwise added DIBALH (1M in toluene, 360 mL, 3 eq) over 2 h. After the reaction mixture was stirred at same temperature for 30 minutes, it was allowed to warm to room temperature. After the reaction was complete, the mixture was quenched by 1N HCl and extracted with EA. The separated organic layer was dried over MgSO4 and evaporated in vacuo to give 2-(3-bromo-4-fluorophenyl)-2-methylpropanal (27 g, 92%). 1H NMR (400 MHz, CDCl3) δ 9.46 (s, 1H), 7.47-7.44 (m, 1H), 7.19-7.15 (m, 1H), 7.12 (t, J=8.4 Hz, 1H), 1.45 (s, 6H).

Workup

  1. customat −78° C.
  2. customover 2 h
  3. customthe mixture was quenched by 1N HCl
  4. extractionextracted with EA
  5. dry with materialThe separated organic layer was dried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c080c04f6b304f7bb1813a6a5be943e8
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…