Borane;tetrahydrofuran → 2,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-methanol

HRID 485545Notes

Reaction equation

HRID 485545 reaction equation
[F:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.B.O1CCCC1>O1CCCC1.C(OCC)C.O>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 128530502,4,5,6-Tetrafluoro-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 202592392,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a dry argon atmosphere 2,4,5,6-tetrafluoro-[1,1'-biphenyl]-3-carboxylic acid (21.6 g, 0.08 mole) was dissolved in 150 ml of tetrahydrofuran with stirring. During a 45 minute period 6.9 g of a borane-tetrahydrofuran complex (1.00 molar solution in tetrahydrofuran) was added to the reaction mixture. After complete addition, the reaction mixture was stirred at room temperature for approximately 23 hours. Water (5 ml) was added slowly to the reaction mixture, and the resultant mixture was stirred for two hours. The mixture was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a residue, which was dissolved in diethyl ether and water. The organic phase was separated, washed with three 200 ml portions of 2N aqueous sodium hydroxide, and dried over anhydrous magnesium sulfate. Filtration of the mixture and evaporation of the solvent from the filtrate gave 2,4,5,6-tetrafluoro-[1,1'-biphenyl]-3-methanol as an oil.

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred at room temperature for approximately 23 hours
  3. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a residue, which
  7. customThe organic phase was separated
  8. washwashed with three 200 ml portions of 2N aqueous sodium hydroxide
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationFiltration of the mixture and evaporation of the solvent from the filtrate

Sources & evidence

ORD record
ord-d0c6a3dcd19242568bd4a455580fcbf5
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Reaction notes

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