Dichloromethane → HCID 86667466, compound

In a 250 mL round bottomed flask, to a solution of ethyl 4-(4-chlorophenyl)-3-oxobutanoate (4.04 g, 16.8 mmol) in methylene chloride (100 mL, 2000 mmol) was added N-bromosuccinimide (3.13 g, 17.6 mmol) and the mixture was stirred for 3 h at room temperature. Reaction was quenched via addition of a 10% aqueous solution of NaHSO3 (50 mL), and the resulting biphasic mixture was vigorously stirred for 15 minutes. The reaction mixture was transferred to a separatory funnel, the layers were separated, and the aqueous layer was extracted with CH2Cl2 (30 mL). The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (50 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford ethyl 2-bromo-4-(4-chlorophenyl)-3-oxobutanoate (5.23 g, yield 97.5%) as a yellow oil that was used without further purification. LC/MS (FA) ES− 317, 319, 321.

1. customReaction
2. customwas quenched via addition of a 10% aqueous solution of NaHSO3 (50 mL)
3. stirringthe resulting biphasic mixture was vigorously stirred for 15 minutes
4. customThe reaction mixture was transferred to a separatory funnel
5. customthe layers were separated
6. extractionthe aqueous layer was extracted with CH2Cl2 (30 mL)
7. washThe combined organic layers were washed with a saturated aqueous solution of NaHCO3 (50 mL)
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-64eb960d53b649528ed8194b8117bf17

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2