Pyridine → 2-(Bromomethyl)-1-benzofuran

HRID 2061344Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.N1C=CC=CC=1.P(Br)(Br)[Br:19]>C1(C)C=CC=CC=1>[Br:19][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Benzofuran-2yl methanol (1.0 g, 6.7 mmol) was dissolved in toluene (50 mL) and pyridine (653 μL, 8.1 mmol) was added. The solution was cooled to 0° C. PBr3 (760 μL, 8.1 mmol) was added dropwise over 15 min. The reaction mixture was then brought up to room temperature and stirred for 1 h. The mixture was washed with K2CO3 solution and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with brine and dried (MgSO4). The solvent was evaporated off in-vacuo and product was purified by flash chromatography, eluting with hexane:EtOAc (4:1) to give 10 (780 mg, 55%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 7.57 (1H, d, J=7.75 Hz, H-4), 7.52 (1H, d, J=8.40, H-7), 7.35 (1H, t, J=8.90, H-4), 7.27 (1H, t, J=8.9 Hz, H-5), 6.79 (1H, s, H-3), 4.64 (2H, s, 2-CH2). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ: 155.34 (C-2), 152.65 (C7a), 129.08 (C3a), 125.20 (C-6), 123.16 (C-5), 121.34 (C—C-4), 111.46 (C-7), 106.30 (C-3), 23.61 (CH2—Br).

Workup

customwas then brought up to room temperature
washThe mixture was washed with K2CO3 solution
extractionextracted with EtOAc (3×30 mL)
washThe EtOAc layer was washed with brine
dry with materialdried (MgSO4)
customThe solvent was evaporated off in-vacuo and product
customwas purified by flash chromatography
washeluting with hexane:EtOAc (4:1)

Sources & evidence

ORD record: ord-49b2954c61b5415ba62b08478b0deac4
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283340B2

Reaction notes

Loading…