Sodium Sulfite → 5-(2-Hydroxyethyl)-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 705874Notes

Reaction equation

HRID 705874 reaction equation
B1C2CCCC1CCC2.[CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[C:16]([CH:19]=1)[C:17]#[N:18])=[CH2:11].[O-:31]S([O-])=O.[Na+].[Na+]>C1COCC1>[OH:31][CH2:11][CH2:10][C:12]1[CH:13]=[CH:14][C:15]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=2)=[C:16]([CH:19]=1)[C:17]#[N:18]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 789669-Borabicyclo(3.3.1)nonaneHCID 668253685-Ethenyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

Product 1

HCID 668255745-(2-Hydroxyethyl)-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrileYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred a solution of 9-BBN (10.37 mL, 5.19 mmol) in dry THF (30 mL) was added dropwise a solution of 5-ethenyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (1 g, 3.46 mmol) in THF (30 mL) under nitrogen at 0° C. for 0.5 h. The mixture was then allowed to warm to room temperature and stirring continued for 2 h. Na2SO3 was added to quench the reaction. Purification via flash chromatography then afforded the title compound (546 mg, 1.777 mmol, 51.4% yield).

Workup

  1. customto quench
  2. customthe reaction
  3. customPurification via flash chromatography

Sources & evidence

ORD record
ord-0cbd7ab325fc45b29540ec040db8c16a
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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