Sodium Carbonate → HCID 1393595, compound

HRID 1879253Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:12][C:13]1[CH:14]=[C:15]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=2)[CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 0.2 M solution of [3-(hydroxymethyl)phenyl]boronic acid in DME were sequentially added 1-bromo-3-iodobenzene (0.83 eq.) and a 2M solution of Na2CO3 (3.0 eq.). The reaction mixture was degassed, trans-bis(triphenylphosphine)palladium(II) chloride (0.01 eq.) was added and it was stirred at 80° C. for 6 h. After cooling down to RT the reaction mixture was diluted with EtOAc and washed with saturated aq. NaHCO3, 1N HCl and brine. The residue was dried (Na2SO4) and evaporated under reduced pressure to afford an oil which was purified by flash chromatography (SiO2, PE:EtOAc=8:2) to afford the title compound 94 as an oil (80%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 7.87 (s, 1H), 7.71 (d, J 7.7, 1H), 7.66 (bs, 1H), 7.59 (t, J 6.8, 2H), 7.47 (t, J 7.7, 2H), 7.39 (d, J 7.7, 1H), 4.61 (s, 2H).

Workup

customThe reaction mixture was degassed
temperatureAfter cooling down to RT the reaction mixture
washwashed with saturated aq. NaHCO3, 1N HCl and brine
dry with materialThe residue was dried (Na2SO4)
customevaporated under reduced pressure
customto afford an oil which
customwas purified by flash chromatography (SiO2, PE:EtOAc=8:2)

Sources & evidence

ORD record: ord-24ffda31d254463b9b2c7c2a8f9e437f
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314062B2

Reaction notes

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