Water → Boma

HRID 7733

Reaction equation

HRID 7733 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[O:18][CH3:19].O.[C-:21]#[N:22].[Na+]>CN(C)C=O>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:21]#[N:22])=[C:4]([O:18][CH3:19])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Product 1

HCID 10192854Boma

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (318 mg, 1 mmol), dimethylformamide (7.5 mL) and deionzed water (2.5 mL) was stirred at rt. Sodium cyanide (150 mg, 3.0 mmol) was added to reaction. After 3 h, dimethylformamide (10 mL) was added to help dissolve solids in reaction mixture. Let reaction mixture stir overnight at rt. Workup was done by washing reaction with brine (3×30 mL), extraction with EtOAc, combined organic extracts, dried (Na2SO4), filtered and removed solvent in vacuo. Flash chromatography of resulting orange solid on silica gel using a gradient elution of 1:9 EtOAc:hexanes to 1:3 EtOAc:hexanes afforded the desired intermediate, [4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile, as a light yellow solid.

Workup

  1. dissolutionto help dissolve solids
  2. customin reaction mixture
  3. customreaction mixture
  4. stirringstir overnight at rt
  5. washby washing
  6. customreaction
  7. extractionwith brine (3×30 mL), extraction with EtOAc
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customremoved solvent in vacuo
  11. customFlash chromatography of resulting orange solid on silica gel using
  12. washa gradient elution of 1:9 EtOAc

Sources & evidence

ORD record
ord-4d49f2de2fea4e568118fe4805b7b8f7
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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