Bromine → HCID 116852751, compound

HRID 518412Notes

Reaction equation

HRID 518412 reaction equation
[Br:1]Br.C([O:6][CH2:7][CH2:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=O)C.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.CC(=O)OCC>[Br:1][C:14]1[CH:13]=[C:12]([S:9]([CH2:8][CH2:7][OH:6])(=[O:11])=[O:10])[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

7

Reactant 4

HCID 24408BromineHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 59224078HCID 59224078, compound

Product 1

HCID 116852751HCID 116852751, compoundYield 29.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

Br2 (25 g, 155.0 mmol) was added dropwise over 30 min to the title compound of step 2 (8.0 g, 31.0 mmol) in acetic acid (100 mL) at 0° C. The mixture was heated at 50° C. for 12 h. Aqueous Na2SO3 (200 mL) was added and the pH was adjusted to 8 with sat. aq. NaHCO3. The mixture was subjected to EA extractive work up and silica gel chromatography (PE: EA=1:0-1:1) to give the title compound (2.7 g, 27.3%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.11 (d, J=2.4 Hz, 1H), 7.87 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 4.05-4.00 (m, 5H), 3.34-3.67 (m, 3H). LCMS: 316.9, 318.9 (M+Na)+

Sources & evidence

ORD record
ord-83d2aceb40344b09bf9436376f5cada9
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

Loading…