Diisobutylaluminum hydride → (6-Bromonaphthalen-2-yl)methanol

HRID 860529Notes

Reaction equation

HRID 860529 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](OCC)=[O:13])[CH:6]=[CH:5]2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][OH:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 1249959Ethyl 6-bromonaphthalene-2-carboxylate

Product 1

HCID 13473070(6-Bromonaphthalen-2-yl)methanolYield 111.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 6-bromo-2-naphthoate (7.90 g, 28.30 mmol) in 200 mL toluene at −78° C. under an atmosphere of argon was added DIBAL (84.9 mL, 1.0 M in toluene, 84.91 mmol) via transfer needle over 20 minutes. After 1 hour the reaction mixture was quenched with ethyl acetate and the resulting mixture was allowed to warm to RT. The mixture was diluted with ethyl acetate and washed with 1.0 N HCl, water and brine. The organics were dried with magnesium sulfate, filtered and evaporated to give 7.51 g of 6-bromo-2-naphthylmethyl alcohol as a white solid and used without further purification in the oxidation (step c). 1H NMR (300 MHz; CDCl3): δ 4.86 (s, 2H); 7.50 (dd, J1=2.0 Hz, J2=8.0 Hz, 1H); 7.57 (d, J=2.0 Hz, 1H); 7.70 (d, J=9.0 Hz, 1H); 7.75 (d, J=8.0 Hz, 1H); 7.79 (s, 1H); 8.00 (d, J=2.0 Hz, 1H).

Workup

  1. customAfter 1 hour the reaction mixture was quenched with ethyl acetate
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with 1.0 N HCl, water and brine
  4. dry with materialThe organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-847c5390e37340c1bc2d0ba46ef50d6b
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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