Water → (1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol

https://huagongshe.com/reaction/602060

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Sulfite	HCID 24437	—
Reactant	1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine	HCID 51003674	—
Reactant	1-Chloro-4-iodo-2-vinylbenzene	HCID 57470606	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	2-Methylpropan-2-ol--water (1/1)	HCID 71401949	—
Product	(1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol	HCID 57470607	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

1-Chloro-4-iodo-2-vinylbenzene (2.43 g, 9.19 mmol) was dissolved in t-BuOH/H2O (1:1, 60 mL) and then cooled to 0° C. AD-mix-α (11 g) was slowly added. The reaction slowly warmed to rt overnight. Sodium sulfite (11 g) was added and the solution stirred at rt. After 3 h, H2O and CH2Cl2 were added and the organic layer isolated. The aqueous layer was washed with CH2Cl2 (3×) and then the combined organic extracts were combined, dried (Na2SO4), concentrated, and purified by Biotage chromatography (0%-100% EtOAc/hexanes) to afford 2.6 g of (1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol as an oil that will solidify over time (95%). 1H NMR (400 MHz, chloroform-d) δ ppm 7.94 (d, J=2.27 Hz, 1 H) 7.55 (dd, J=8.34, 2.02 Hz, 1 H) 7.07 (d, J=8.34 Hz, 1 H) 5.17 (dd, J=7.58, 3.03 Hz, 1 H) 3.90 (dd, J=11.24, 3.16 Hz, 1 H) 3.54 (dd, J=11.24, 7.71 Hz, 1 H) 3.49 (s, 2 H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07902394B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-46901b69b89d41918febd22302ea0be4
Source note	uspto-grants-2011_03