Ethanol → HCID 66718910, compound

HRID 1525899Notes

Reaction equation

HRID 1525899 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([F:10])[CH:3]=1.[C-]#[N:12].[Na+].[CH2:14]([OH:16])C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:14]([NH2:12])=[O:16])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 66718910HCID 66718910, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (56.0 mmol) in ethanol (75.0 ml) and water (15.0 ml) was added sodium cyanide (67.2 mmol). The reaction was refluxed for 3 days then cooled and diluted with water. The solids were collected, slurried in water (100 mL) and 6N aq HCl (50 mL) for 1 h, and then filtered and dried via suction. The collected solids were slurried again in dichloromethane, and the solids were collected and dried to afford 2-(4-bromo-2-fluorophenyl)acetamide (6.9 g, 52% yield) as a white solid. The dichloromethane filtrate was evaporated to afford a crude mixture (72% purity by LCMS) of the title product and 2-(4-bromo-2-fluorophenyl)acetamide (1.4:1 ratio) as a light yellow solid (4.5 g). A portion of this mixture was used directly in the next step. Title product: MS(ES)+ m/e 214.0, 216.2 [M+H]+.

Workup

  1. temperatureThe reaction was refluxed for 3 days
  2. temperaturethen cooled
  3. customThe solids were collected
  4. filtrationfiltered
  5. customdried via suction
  6. customthe solids were collected
  7. customdried

Sources & evidence

ORD record
ord-ff6f4c7dcf464923961c5d6bd7c9b55e
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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