Water → HCID 59656639, compound

HRID 2054902Notes

Reaction equation

HRID 2054902 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:22]1([CH2:27][OH:28])[CH2:26][CH2:25][CH2:24][CH2:23]1.O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:6]#[N:7])=[C:8]([O:28][CH2:27][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77195CyclopentanemethanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27569164-Bromo-2,6-difluorobenzonitrile

Product 1

HCID 59656639HCID 59656639, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the above benzonitrile intermediate (7.5 g, 34.4 mmol) in dry THF (50 mL) at 0° C. was added a mixture of sodium bis(trimethylsilyl)amide (1.0 M, 34 mL, 34 mmol) and cyclopentanemethanol (3.4 g, 34 mmol) in THF (100 mL). The reaction was allowed to warm up to room temperature and stirred overnight. Water (50 mL) was added to the reaction and the product was extracted by CH2Cl2 (2×50 mL). The solvent was washed with brine and dried over Na2SO4. The solvent was removed to give 4-bromo-2-cyclopentylmethoxy-6-fluorobenzonitrile (4.5 g, 43.9%).

Workup

  1. extractionthe product was extracted by CH2Cl2 (2×50 mL)
  2. washThe solvent was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-0babfa298ad34290820823be02ba4102
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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