Boron trifluoride etherate → HCID 90253497, compound

HRID 1478769Notes

Reaction equation

B(F)(F)F.[CH3:5][CH2:6][O:7][CH2:8][CH3:9].[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1I.[CH2:19]([Li])[CH2:20][CH2:21][CH3:22].[Cl-].[NH4+:25].[C:26]([O:29]CC)(=O)[CH3:27]>C1(C)C=CC=CC=1>[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:9]12[CH2:8][O:7][CH:6]([C@@H:20]3[CH2:19][C@H:21]3[CH3:22])[CH2:5][CH:27]1[CH2:26][O:29][NH:25]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of C85 (2.58 g, 14.2 mmol) in toluene (50 mL) cooled to −78° C. was added boron trifluoride diethyl etherate (4.23 mL, 15.9 mmol) drop-wise. After stirring for 30 minutes at −78° C., 2,4-difluoro-1-iodobenzene (3.90 g, 15.9 mmol) was added, followed by drop-wise addition of n-butyllithium (2.5 M in hexanes, 6.04 mL, 15.1 mmol). The reaction was stirred at −78° C. for 90 minutes at which point saturated aqueous ammonium chloride solution (10 mL) was added. The reaction was allowed to warm to room temperature and then taken up in ethyl acetate. The organic layer was washed with water and with saturated aqueous sodium chloride solution and then concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 25% ethyl acetate in heptane) provided the product as a colorless oil. Yield: 1.25 g, 4.23 mmol, 30%. LCMS m/z 296.2 [M+H+]. 1H NMR (400 MHz, CDCl3): characteristic peaks δ 7.82-7.88 (m, 1H), 6.79-6.84 (m, 1H), 6.68-6.74 (m, 1H), 3.93-3.97 (m, 1H), 3.72-3.76 (m, 1H), 3.63-3.66 (m, 1H), 3.44-3.48 (m, 1H), 2.83-2.98 (m, 1H), 1.83-1.92 (m, 1H), 1.44-1.59 (m, 1H), 0.99-1.01 (m, 1H), 0.72-0.87 (m, 1H).

Workup

additionwas added
temperatureto warm to room temperature
washThe organic layer was washed with water and with saturated aqueous sodium chloride solution
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4b109b0f02b64d3e89e40f1bcc091169
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403846B2

Reaction notes

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