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

Participants

Role	Name	HCID	Charge
Reactant	1,2-Ethanedithiol	HCID 10902	—
Reactant	Sodium borohydride	HCID 4311764	—
Reactant	Methyl 3-chloro-4-cyano-2-methylbenzoate	HCID 68579417	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile	HCID 68577571	66.5%

Reaction Conditions

Temperature	70 °C

Reaction Steps

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]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696241B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-6f973348b7b245bc91aa790a6ac3c759
Source note	uspto-grants-2010_04