Water → 2-Fluoro-4-(2-hydroxyethyl)benzonitrile

HRID 1465784Notes

Reaction equation

HRID 1465784 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1.O>C1COCC1>[F:15][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][OH:4])[CH:12]=[CH:11][C:10]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 58915197Methyl 2-(4-cyano-3-fluorophenyl)acetate

Product 1

HCID 666441972-Fluoro-4-(2-hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (1.94 mL, 3.88 mmol, 2 M in THF) was added to a stirred solution of methyl(4-cyano-3-fluorophenyl)acetate (0.50 g, 2.59 mmol) in THF (25 ml) at 0° C. The resulting solution was stirred for 12 h. Water (10 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. The residue was purified by column chromatography eluting with EtOAc-Hexanes (7:3→1:1) to give the product as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.60 (dd, J=7.4, J=7.1 Hz, 1H), 7.30 (s, 1H), 7.18 (dd, J=7.3, J=9.1 Hz, 1H), 3.95 (t, J=6.2 Hz, 2H), 2.93 (t, J=6.3 Hz, 2H).

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. customThe residue was purified by column chromatography
  6. washeluting with EtOAc-Hexanes (7:3→1:1)

Sources & evidence

ORD record
ord-570592389ae543ff8172cb6593da852f
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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