Hydrochloric Acid → HCID 22008085, compound

HRID 321900Notes

Reaction equation

HRID 321900 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18]COC)=[C:14]([F:22])[CH:13]=1.FC1C(F)=C(CCC)C=CC=1I.OB(O)C1C=CC(OCOC)=C(F)C=1.Cl>[Pd].O.CO>[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:22])[CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 22008075HCID 22008075, compoundHCID 22008077HCID 22008077, compoundHCID 22008084HCID 22008084, compound

Product 1

HCID 22008085HCID 22008085, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Solution of 10.0 g (32.2 mmol) of 2,3,3′-trifluoro-4′-methoxymethoxy-4-propylbiphenyl [prepared by cross coupling reaction of 2,3-difluoro-4-propyliodobenzene with dihydroxy(3-fluoro-4-methoxymethoxyphenyl)borane in the presence of a Pd catalyst], 50 ml of methanol, and 10 ml of a concentrated hydrochloric acid was heated to reflux for 3 hours. Water in an amount of 50 ml was added to the reaction liquid and subjected to extraction with 100 ml of diethyl ether. After the organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution twice and water thrice, it was dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure to obtain 8.5 g of a crude 2,3,3′-trifluoro-4′-hydroxy-4-propylbiphenyl. (Yield: 99.8%)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. extractionsubjected to extraction with 100 ml of diethyl ether
  4. customAfter the organic layer thus obtained
  5. washwas washed with a diluted aqueous sodium bicarbonate solution twice
  6. dry with materialwater thrice, it was dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-62e0a4f147c143a29a11d616ba965282
Source dataset
uspto-grants-2001_04
Patent number
US06210761B1

Reaction notes

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