Water → HCID 11301861, compound

HRID 1666747Notes

Reaction equation

Br[C:2]1[C:11]([OH:12])=[C:10]([CH3:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6]([CH3:16])([CH3:15])[O:7]2.[N+:17]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18].O>COCCOC.C([O-])([O-])=O.[Na+].[Na+].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>[CH3:15][C:6]1([CH3:16])[CH2:5][CH2:4][C:3]2[C:8](=[C:9]([CH3:14])[C:10]([CH3:13])=[C:11]([OH:12])[C:2]=2[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:17]([O-:19])=[O:18])[CH:25]=2)[O:7]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-bromo-2,2,7,8-tetramethyl-chroman-6-ol (400 mg, 1.40 mmol), 3-nitrophenyl boronic acid (300 mg, and Pd(PPh3)4 (100 mg, 5% mol) in glycol dimethyl ether (DME, 20 mL) and 2M Na2CO3 solution (5 mL) was stirred at 120° C. for 3-5 h. After pouring it into water, the mixture was extracted with EtOAc. The EtOAc layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 10% EtOAc in hexane to give a yellow solid (140 mg). 1H NMR (300 MHz, CDCl3): 8.25-8.16 (μ, 2H), 6.76 (μ, 2H), 4.13 (σ, 1H, OH), 2.27 (μ, 2H), 2.21, 2.19 (2σ, 6H), 1.68 (μ, 2H), 1.32 (σ, 6H) ppm. 13C NMR (75 MHz, CDCl3) δ: 167.36, 148.79, 145.85, 143.34, 138.27, 136.95, 130.10, 126.51, 125.56, 122.76, 122.29, 115.84, 73.10, 32.83, 27.07, 26.71, 12.95, 12.24, 12.14 ppm. MS: m/z: 328 (MH+).

Workup

extractionthe mixture was extracted with EtOAc
washThe EtOAc layer was washed with water
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
washeluting with 10% EtOAc in hexane

Sources & evidence

ORD record: ord-64b331d1666549e8b1386148e3ddd6b9
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044097B2

Reaction notes

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