Hydrochloric Acid → 2-Bromo-5-(trifluoromethyl)benzaldehyde

HRID 1191919Notes

Reaction equation

HRID 1191919 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#N.[H-].C([Al+]CC(C)C)C(C)C.CC[O:26]CC.Cl>ClCCl.CCCCCC>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 122239802-Bromo-5-(trifluoromethyl)benzonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 70180472-Bromo-5-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-bromo-5-(trifluoromethyl)benzonitrile (10.0 g, 40 mmol) in dichloromethane (100 mL) was dropwise added a 1.0 M solution of diisobutylaluminum hydride in hexane (48 mL). The resulting solution was stirred under nitrogen at ambient temperature for 1 h and was then diluted by addition of ether (100 mL). After cooling in an ice bath, a 3 N solution of HCl was carefully added, and the mixture was vigorously stirred at ambient temperature for 15 min. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting oil was purified by flash chromatography (5% EtOAc/hexane) affording 5 g of 2-bromo-5-trifluoromethylbenzaldehyde. 1H NMR (CDCl3) δ 10.39 (s, 1H), 8.18 (d, J=2 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.70 (dd, J=8.5 Hz, 2 Hz, 1H).

Workup

  1. temperatureAfter cooling in an ice bath
  2. stirringthe mixture was vigorously stirred at ambient temperature for 15 min
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe resulting oil was purified by flash chromatography (5% EtOAc/hexane)

Sources & evidence

ORD record
ord-45767fc6229b48d2a53908b81616730a
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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