Hydrochloric Acid → 6-Bromonaphthalene-2-carbaldehyde

HRID 1925261Notes

Reaction equation

HRID 1925261 reaction equation
CON(C)[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:16])[CH:12]=2)[CH:7]=1)=[O:5].CC(C[AlH]CC(C)C)C.Cl>C1COCC1>[Br:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH:4]=[O:5])[CH:15]=[CH:14]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 598132256-bromo-N-methoxy-N-methyl-2-Naphthalenecarboxamide

Product 1

HCID 134770296-Bromonaphthalene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-bromo-naphthalene-2-carboxylic acid methoxy-methyl-amide (Step c, 6.3 g, 21.4 mmol) in THF (200 mL) at −78° C., DIBAL (1M in THF, 25.7 mL, 25.7 mmol) was added. The mixture was stirred at −78° C. for 10 min, warmed to RT and stirred for 2 h. The reaction was poured into 1N HCl and extracted with EtOAc 3×. The combined organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel column chromatography with (5-20% EtOAc/hexane) to give the titled compound as a white solid. MS (ESI, pos. ion) m/z: 236.0 (M+1).

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for 2 h
  3. extractionextracted with EtOAc 3×
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica gel column chromatography with (5-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-fb008dc4ebca4f0db4539d454e8cb443
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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