Water → HCID 65489737, compound

HRID 1364381Notes

Reaction equation

HRID 1364381 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:14]=1[C:15]#[N:16].O>CN(C=O)C>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:9][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([I:3])=[CH:5][CH:6]=2)[C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 290124-Iodobenzyl alcoholHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 65489737HCID 65489737, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%; 432 mg; 10.8 mmol) was suspended in DMF (5 mL) and cooled to 0° C. under inert atmosphere. 4-Iodobenzyl alcohol (2.53 g; 10.8 mmol) was dissolved in DMF (5 mL) and added dropwise to the sodium hydride mixture. The solution was allowed to warm to room temperature and stirred for 15 minutes. The solution was then cooled to 0° C. 2,6-Difluorobenzonitrile (1 g; 7.2 mmol) in DMF (20 mL) was added dropwise to the alcohol solution and stirred for 2 hours. The solution was poured over 100 mL of cooled water. The solution was cooled for 1 hour and a precipitate was evident. The solid was collected by vacuum filtration and washed with water. Purification by recrystallization in cyclohexane yielded 1.49 grams of 2-fluoro-6-(4-iodobenzyloxy)benzonitrile.

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe solution was then cooled to 0° C
  3. stirringstirred for 2 hours
  4. temperatureThe solution was cooled for 1 hour
  5. filtrationThe solid was collected by vacuum filtration
  6. washwashed with water
  7. customPurification
  8. customby recrystallization in cyclohexane

Sources & evidence

ORD record
ord-569e61cfad78441cb9889ad5c06edc7a
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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