Borane → (3-Bromophenanthren-9-YL)methanol

HRID 1646050Notes

Reaction equation

HRID 1646050 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([C:16](O)=[O:17])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.B>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][OH:17])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 6331BoraneHCID 126158193-Bromophenanthrene-9-carboxylic acid

Product 1

HCID 15159129(3-Bromophenanthren-9-YL)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-bromo-phenanthrene-9-carboxylic acid (6.27 g, 20.8 mmol) in 100 ml of THF was cooled to 0° C. and a solution of borane in THF (1.0M, 25 ml, 25 mmol) was added dropwise. The cooling bath was removed, and the solution was stirred at room temperature for 19 hours and was then quenched by the cautious addition of methanol (25 ml). The solution was evaporated to dryness in vacuo and the residue was dissolved in methanol--CH2Cl2 (1:1) and again evaporated. After one repetition of this dissolution-evaporation process, 5.96 g (100%) of the title compound was obtained as a brown solid which was used in the next reaction without purification.

Workup

  1. customThe cooling bath was removed
  2. customwas then quenched by the cautious addition of methanol (25 ml)
  3. customThe solution was evaporated to dryness in vacuo
  4. dissolutionthe residue was dissolved in methanol--CH2Cl2 (1:1)
  5. customagain evaporated

Sources & evidence

ORD record
ord-221466c856ce4b57b3a9390805984f74
Source dataset
uspto-grants-1993_01
Patent number
US05177202

Reaction notes

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