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

HRID 1627363Notes

Reaction equation

HRID 1627363 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-4238516eb3c24df29d218390a6124d72
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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