Sodium Carbonate → Ethyl acetate hexane

HRID 511950Notes

Reaction equation

Br[C:2]1[C:11]2C(=C([N+]([O-])=[O:13])C=C[CH:10]=2)[CH:5]=[C:4](OC)[C:3]=1OC.C(C1C=CC(B(O)O)=CC=1)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].[O:38]1[CH2:43][CH2:42]O[CH2:40][CH2:39]1>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:40][CH2:39][O:38][C:43]([CH3:42])=[O:13].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 100 °C

Procedure

1-Bromo-2,3-dimethoxy-5-nitronaphthalene (1 g), 4-t-butylphenylboronic acid (685 mg, 1.2 eq.), Pd(PPh3)4 (370 mg, 0.1 eq.), and Na2CO3 (680 mg, 2 eq.) were combined in a flask with 20 mL dioxane and 5 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. overnight. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 20% EtOAc/hexane yielding product as a yellow solid (1.159 g, 99% yield). 1H NMR (400 MHz) (CDCl3) δ 8.18 (dd, J=8 Hz, J=4 Hz, 1H), 8.08 (s, 1H), 7.79-7.77 (m, 1H), 7.54 (dt, J=8 Hz, J=4 Hz, 2H), 7.30 (t, J=4 Hz, 1H), 7.28-7.27 (m, 2H), 3.99 (s, 3H), 3.58 (s, 3H), 1.34 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 155.05, 150.69, 147.53, 145.44, 132.89, 132.72, 131.97, 130.66, 130.06, 125.26, 123.59, 123.54 121.87, 102.16, 61.08, 55.91, 34.71, 31.43.

Workup

customdegassed
customReaction mixture
temperatureSolution was cooled to room temperature
washwashed with saturated NaHCO3
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-7fc8ea92a5b3488e8717fa2888149147
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102617B2

Reaction notes

Loading…