Diisobutylaluminum hydride → HCID 59157962, compound

HRID 1920515Notes

Reaction equation

HRID 1920515 reaction equation
[Br:1][C:2]1[C:11]([I:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](OC)=[O:14])=[CH:7]2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:11]([I:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][OH:14])=[CH:7]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59157934HCID 59157934, compound

Product 1

HCID 59157962HCID 59157962, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 5-bromo-6-iodo-2-naphthoate (0.37 g, 0.95 mmol) in toluene (10 mL) at −78° C. was added DIBAL (3 mL of a 1M solution in PhMe, 3 mmol) dropwise. The temperature was raised to 0° C. for 1 h. The reaction was quenched with 10 mL of 1M HCl, extracted with EtOAc and dried over Na2SO4. The organic extracts were evaporated to dryness to afford the titled compound.

Workup

  1. customThe reaction was quenched with 10 mL of 1M HCl
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customThe organic extracts were evaporated to dryness

Sources & evidence

ORD record
ord-78dfa368984f49c4ae62fd7b6cfdb944
Source dataset
uspto-grants-2012_05
Patent number
US08168815B2

Reaction notes

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