Dimethyl Sulfoxide → Ethyl 5-bromo-2,3-dihydro-1H-indene-2-carboxylate

HRID 1057152Notes

Reaction equation

[Cl-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](C(OCC)=O)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]2.CS(C)=O>O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]2

Participants

Conditions

Temperature: 160 °C

Procedure

Lithium chloride (66 mg, 1.55 mmol) was added to a solution of diethyl 5-bromo-1H-indene-2,2(3H)-dicarboxylate (200 mg, 0.58 mmol), DMSO (2 mL), and H2O (0.2 mL). The mixture was stirred overnight at 160° C. After cooled to room temperature, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (2×20 mL), dried over MgSO4 and concentrated in vacuo to afford the title compound (120 mg, 76%). 1HNMR (400 MHz, DMSO-d6): δ 7.42 (s, 1H), 7.31 (d, 1H), 7.18 (d, 1H), 4.10 (q, 2H), 3.39-3.34 (m, 1H), 3.17-3.01 (m, 4H), 1.19 (t, 3H).

Workup

temperatureAfter cooled to room temperature
extractionextracted with EtOAc (3×15 mL)
washThe combined organic layers were washed with saturated aqueous NaHCO3 (2×20 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2743ec6f15124f55a54f31824387976d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399646B2

Reaction notes

Loading…