1,2-Ethanedithiol → 2-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile

HRID 642748

Reaction equation

HRID 642748 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[N:13])[C:5](OC)=[O:6].C(S)CS.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 4311764Sodium borohydrideHCID 68579417Methyl 3-chloro-4-cyano-2-methylbenzoate

Product 1

HCID 685775712-Chloro-4-(hydroxymethyl)-3-methylbenzonitrileYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a pressure reaction flask containing compound 7A (1.5 g, 7.2 mmol) in THF (30 mL) were added 1,2-ethanedithiol (2.4 g, 28.6 mmol) and NaBH4 (812 mg, 21.5 mmol). It was sealed, and heated at 70° C. for 2 hr, and cooled to RT. The reaction mixture was concentrated, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Recrystallization in EtOAc/hexanes give the title compound (870 mg). (ES) m/z 182 [M+H]+; 204 [M+Na]+.

Workup

  1. customTo a pressure reaction flask
  2. customIt was sealed
  3. temperaturecooled to RT
  4. concentrationThe reaction mixture was concentrated
  5. dissolutiondissolved in EtOAc
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customRecrystallization in EtOAc/hexanes

Sources & evidence

ORD record
ord-6f973348b7b245bc91aa790a6ac3c759
Source dataset
uspto-grants-2010_04
Patent number
US07696241B2

Linked notes

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