Hydrochloric Acid → 2-Bromo-4-hydroxybenzaldehyde

HRID 716806Notes

Reaction equation

HRID 716806 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#N.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.Cl.C1C[O:32]CC1>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:32]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8028TetrahydrofuranHCID 130422512-Bromo-4-hydroxybenzonitrile2×HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 110848662-Bromo-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-bromo-4-hydroxy-benzonitrile (Intermediate 7, 2000 mg, 10.1 mmol) in DCM (50 mL) and THF (10 mL), at 0° C., diisobutylaluminum hydride 1M in toluene (20.2 ml, 20.2 mmol) was slowly added (10 min) and the reaction mixture was stirred at the same temperature for 1 hour. Then 40 ml of HCl 2M were added and the reaction mixture was warmed at 40° C. for 30 minutes. After cooling ethyl acetate (100 ml) was added and two phases were separated. The organic layer was washed with brine (3×100 ml) dried over sodium sulphate and concentrated under vacuum to give the title compound (1950 mg) which was used in the next step without further purification.

Workup

  1. additionwas added
  2. customtwo phases were separated
  3. washThe organic layer was washed with brine (3×100 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6bd3287dc33b418e83203ceef8eb8dac
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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