Water → 2-(5-Bromo-7-chlorobenzofuran-2-yl)ethanamine

HRID 2179401Notes

Reaction equation

[N:1]([CH2:4][CH2:5][C:6]1[O:7][C:8]2[C:14]([Cl:15])=[CH:13][C:12]([Br:16])=[CH:11][C:9]=2[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Br:16][C:12]1[CH:13]=[C:14]([Cl:15])[C:8]2[O:7][C:6]([CH2:5][CH2:4][NH2:1])=[CH:10][C:9]=2[CH:11]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of the product of step D (500 mg, 1.66 mmol) in THF (8 mL) was added triphenylphosphine (72 mg, 3.32 mmol) followed by water (3 mL). The reaction mixture was heated to 65° C. for 4 h and concentrated in vacuo. Purification by column chromatography (SiO2, 95:5 dichloromethane/methanol) provided 2-(5-bromo-7-chlorobenzofuran-2-yl)ethanamine (388 mg, 85%) as a colorless liquid: 1H NMR (CDCl3, 400 MHz) δ 7.51 (t, J=2.4 Hz, 1H), 7.36 (t, J=2.4 Hz, 1H), 6.45 (s, 1H), 3.12 (t, J=8.4 Hz, 2H), 2.94 (t, J=8.8 Hz, 2H).

Workup

concentrationconcentrated in vacuo
customPurification by column chromatography (SiO2, 95:5 dichloromethane/methanol)

Sources & evidence

ORD record: ord-40dcd9f1b2e4473ca35399449a861720
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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