1-Bromooctane → HCID 14817232, compound

HRID 358811Notes

Reaction equation

HRID 358811 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[OH-].[K+].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([O:10][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 14817232HCID 14817232, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

60 g of 3-fluoro-4-cyanophenol and 16 g of potassium hydroxide were dissolved in a solvent mixture of 600 ml of ethanol and 60 ml of water. To the resulting solution, was added dropwise 55.8 g of octyl bromide. After the completion of the addition, the obtained mixture was refluxed for six hours and then allowed to cool to room temperature. The solvent was distilled off and 300 ml of ethyl acetate was added to the residue. The organic layer was washed with water until the aqueous layer became neutral. The organic layer was dehydrated over anhydrous sodium sulfate and the solvent was distilled off. After purifying by distillation (main fraction: 0.5 mmHg, 157° to 160° C.), 63 g of 2-fluoro-4-octyloxybenzonitrile was obtained. Yield: 58%. 63 g of the 2-fluoro-4-octyloxybenzonitrile thus obtained was dissolved in 70 ml of absolute ether and 12.7 g of absolute ethanol was added thereto. The obtained mixture was cooled to -10° C. Then hydrogen chloride gas was bubbled therein for 30 minutes under stirring. After confirming that no hydrogen chloride was absorbed any more, the mixture was stirred at room temperature for 72 hours. 400 ml of absolute ether was added to the mixture. The crystals thus precipitated were filtered and vacuum-dried to thereby give 42 g of imino ester hydrochloride. Yield: 52%.

Workup

  1. additionAfter the completion of the addition
  2. temperaturethe obtained mixture was refluxed for six hours
  3. distillationThe solvent was distilled off
  4. addition300 ml of ethyl acetate was added to the residue
  5. washThe organic layer was washed with water until the aqueous layer
  6. distillationthe solvent was distilled off
  7. distillationAfter purifying by distillation (main fraction: 0.5 mmHg, 157° to 160° C.)

Sources & evidence

ORD record
ord-db4849686f43478b87b7cd2a2167d3f2
Source dataset
uspto-grants-1991_03
Patent number
US04997942

Reaction notes

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