Borane → HCID 19432446, compound

HRID 1886700Notes

Reaction equation

HRID 1886700 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14](O)=[O:15])=[CH:13][C:8]=3[O:7][C:6]=2[CH:17]=1.B>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14][OH:15])=[CH:13][C:8]=3[O:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 19432430HCID 19432430, compound

Product 1

HCID 19432446HCID 19432446, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cloudy solution of 3-bromo-dibenzofuran-7-carboxylic acid (3.2 g, 10.9 mmol) in 80 ml THF was cooled to 0° C. and a solution of borane in THF (1.0M, 13.0 ml, 13.0 mmol) was added dropwise. The cooling bath was removed and the reaction was stirred at room temperature for 20 hours and was then quenched by the cautious addition of methanol (10 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, 2.74 g (90%) of the title compound was obtained as a brown solid and used in the next reaction without purification.

Workup

  1. customThe cooling bath was removed
  2. customwas then quenched by the cautious addition of methanol (10 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-0396996454b14c49abe5a119f0abddfc
Source dataset
uspto-grants-1992_09
Patent number
US05151512

Reaction notes

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