Sodium borohydride → 2-Fluoro-4-(hydroxymethyl)benzonitrile

HRID 1348900Notes

Reaction equation

HRID 1348900 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][C:4]=1[F:13])#[N:2].[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>C1COCC1.C(O)C>[F:13][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[CH:12][C:3]=1[C:1]#[N:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 17965941Methyl 4-cyano-3-fluorobenzoate

Product 1

HCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 52A (1.0 g, 5.58 mmol) in THF (20 mL) at room temperature was treated with a solution of CaCl2 (1.24 g, 11.16 mmol) in ethanol (20 mL). The resulting solution was treated with NaBH4 (845 mg, 22.33 mmol) over 20 minutes, stirred for 1.25 hours, then slowly quenched with saturated ammonium chloride (100 mL), and concentrated. The remaining aqueous portion was extracted with ethyl acetate (3×100 mL) and the combined extracts were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (APCI) m/z 169 (M+NH4)+; 1H NMR (300 MHz, CDCl3) δ 7.60 (t, 1H), 7.29-7.23 (m, 2H), 4.80 (s, 2H).

Workup

  1. customslowly quenched with saturated ammonium chloride (100 mL)
  2. concentrationconcentrated
  3. extractionThe remaining aqueous portion was extracted with ethyl acetate (3×100 mL)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fd8118ff7b6345f88d65e12b503fc932
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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