Hydrochloric Acid → 2-(3-Bromo-4-methoxyphenyl)-2-methylpropanal

HRID 1989816Notes

Reaction equation

HRID 1989816 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([CH3:14])([CH3:13])[C:11]#N)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CC(C[AlH]CC(C)C)C.Cl.C1C[O:28]CC1>>[Br:1][C:2]1[CH:3]=[C:4]([C:10]([CH3:14])([CH3:13])[CH:11]=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 113688102-(3-Bromo-4-methoxyphenyl)-2-methylpropionitrile

Product 1

HCID 111611902-(3-Bromo-4-methoxyphenyl)-2-methylpropanal

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-bromo-4-methoxy-phenyl)-2-methyl-propionitrile (12.71 g, 0.050 mol) in dry THF (100 mL) was cooled to −10° C. under argon. DIBALH (1M in THF, 100 mL, 0.10 mol) was added keeping the temperature below 0° C. The mixture was stirred for 30 min/0° C. and then 2 h/25° C. The clear solution was carefully poured into icecold hydrochloric acid (2M, 100 mL). The THF was removed under reduced pressure to give clear oil. The oil was destilled (b.p. 114-130° C./4.3×10−3 mbar) Yield: 7.40 g (58%). GCMS: >99%

Workup

  1. customthe temperature below 0° C
  2. custom2 h/25° C
  3. customThe THF was removed under reduced pressure
  4. customto give clear oil

Sources & evidence

ORD record
ord-fd5e346edf9b4989920558fb33e2bd91
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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