Hydrochloric Acid → 3-Bromo-7-(hydroxymethyl)-phenanthrene

HRID 1084327Notes

Reaction equation

HRID 1084327 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH2:16][O:17]C(=O)C)[CH:9]=3.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.Cl>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH2:16][OH:17])[CH:9]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 151591383-Bromo-7-(acetoxymethyl)phenanthreneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 151591393-Bromo-7-(hydroxymethyl)-phenanthreneYield 99.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromo-7-(acetoxymethyl)-phenanthrene (2.042 g, 6.20 mmol) in 50 ml of THF was cooled to 0° C. and a solution of diisobutylaluminum hydride in hexane (1.0M, 14 ml, 14 mmol) was added dropwise. After 30 minutes, the solution was cautiously hydrolyzed with 1N HCl and was then diluted with ethyl acetate and washed successively with 1N HCl, sat. NaHCO3, H2O, and brine. Drying (MgSO4) and evaporation gave 1.77 g (99%) of the title compound as a white solid which was used in the next reaction without purification.

Workup

  1. washwashed successively with 1N HCl, sat. NaHCO3, H2O, and brine
  2. customDrying
  3. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-1297733f5b604ba69c185a5da9360ae6
Source dataset
uspto-grants-1991_04
Patent number
US05004740

Reaction notes

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