Borane → HCID 21945613, compound

HRID 1449231Notes

Reaction equation

HRID 1449231 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([C:11](O)=[O:12])[C:3]=1[C:14](O)=[O:15].B>O1CCCC1>[F:1][C:2]1[C:3]([CH2:14][OH:15])=[C:4]([CH2:11][OH:12])[C:5]([F:10])=[C:6]([F:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6331BoraneHCID 695443,4,5,6-Tetrafluorophthalic acid

Product 1

HCID 21945613HCID 21945613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 10 tetrahydrofuran (THF) is added 3,4,5,6-tetrafluoro-1,2-benzenedicarboxylic acid (2 g, 8.4 mmol). After cooling at 0°, 21.0 ml (20.9 mmol) of 1 M borane in THF is slowly added. The reaction mixture is allowed to rise to RT and stirred at RT for 18 hours and then is cooled and quenched with 10% HCl. The reaction mixture is added to ether, and the organic phase is washed with water, sat. sodium bicarbonate and brine, dried over sodium sulfate and evaporated under vacuum to yield 3,4,5,6-tetrafluoro-1,2-bis(hydroxymethyl)benzene.

Workup

  1. temperatureAfter cooling at 0°
  2. customto rise to RT
  3. temperatureis cooled
  4. customquenched with 10% HCl
  5. additionThe reaction mixture is added to ether
  6. washthe organic phase is washed with water, sat. sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-e03375cfff6f4d529583287f2e2c8dd1
Source dataset
uspto-grants-1980_02
Patent number
US04189598

Reaction notes

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