Water → 2,5-Difluoro-4-(2-hydroxyethyl)benzonitrile

HRID 1519529Notes

Reaction equation

HRID 1519529 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([C:14]#[N:15])=[CH:9][C:8]=1[F:16].O>C1COCC1>[F:13][C:11]1[CH:12]=[C:7]([CH2:6][CH2:5][OH:4])[C:8]([F:16])=[CH:9][C:10]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 86694454Methyl 2-(4-cyano-2,5-difluorophenyl)acetate

Product 1

HCID 675172212,5-Difluoro-4-(2-hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (1.45 mL, 2.9 mmol, 2 M in THF) was added to a stirred solution of methyl(4-cyano-2,5-difluorophenyl)acetate (0.47 g, 2.2 mmol) in THF (25 ml) at 0° C. The resulting solution was stirred for 12 h. Water (15 ml) was added, and the resulting solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure to yield the product after purification on silica gel (eluted with 5-30% ethyl acetate-hexanes) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.32 (dd, J=5.3, J=5.0 Hz, 1H), 7.23 (dd, J=5.8, J=5.7 Hz, 1H), 3.95 (t, J=6.2, J=6.4 Hz, 2H), 2.98 (t, J=6.4, J=6.2 Hz, 2H). LC-MS (IE, m/z): 184 [M+1]+.

Workup

  1. extractionthe resulting solution was extracted with dichloromethane (2×50 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto yield the product
  6. customafter purification on silica gel (eluted with 5-30% ethyl acetate-hexanes) as a clear oil

Sources & evidence

ORD record
ord-3d1fc497f1fd4ef3bb30470309277dac
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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