Methanol → 2-Bromo-6-chloro-3-ethoxy-4-(1-hydroxyethyl)benzonitrile

HRID 1499736Notes

Reaction equation

HRID 1499736 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:13]=[C:12]([Cl:14])[C:9]([C:10]#[N:11])=[C:8]([Br:15])[C:7]=1[O:16][CH2:17][CH3:18])(=[O:5])[CH3:4].CO>>[Br:15][C:8]1[C:7]([O:16][CH2:17][CH3:18])=[C:6]([CH:3]([OH:5])[CH3:4])[CH:13]=[C:12]([Cl:14])[C:9]=1[C:10]#[N:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866668914-Acetyl-2-bromo-6-chloro-3-ethoxybenzonitrile

Product 1

HCID 866776662-Bromo-6-chloro-3-ethoxy-4-(1-hydroxyethyl)benzonitrileYield 100%

Procedure

Sodium tetrahydroborate (38 mg, 0.99 mmol) was added to a mixture of 4-acetyl-2-bromo-6-chloro-3-ethoxybenzonitrile (200 mg, 0.7 mmol) in methanol (5 mL, 100 mmol) at 0° C. The reaction was stirred at room temperature for 1 hour, concentrated and partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give crude 2-bromo-6-chloro-3-ethoxy-4-(1-hydroxyethyl)benzonitrile as a clear oil (0.15 gm, 100%), LCMS calculated for C11H11BrClNO2(M+H)+: m/z=303.9, 305.9; found: 304.0, 305.9.

Workup

  1. concentrationconcentrated
  2. custompartitioned between water and EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-24609a5223c34cd78a78f558af13fca8
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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