Butyl ether → HCID 12140011, compound

HRID 2266978Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

Reactant 4

HCID 8909Butyl ether

HCID 97314-Fluoroaniline

HCID 121674-Chloroanisole

HCID 23676156Sodium t-butoxide

Product 1

HCID 12140011HCID 12140011, compoundYield 96.2%

Conditions

Temperature: 110 °C

Procedure

Following general procedure E, a mixture of 4-chloroanisole (123 μL, 1.0 mmol), 4-fluoroaniline (114 μL, 1.2 mmol), NaOt-Bu (115 mg, 1.2 mmol), 10 (0.08 mg, 0.01 mol %), 1 (0.05 mg, 0.01 mol %), and Bu2O (1 mL) was heated to 110° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes) to provide the title compound as a white solid (209 mg, 94%), mp 59-60° C. 1H NMR (300 MHz, CDCl3) δ: 7.03-6.86 (m, 8H), 5.41 (s, 1H), 3.81 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 159.0, 155.8, 155.2, 141.4, 136.8, 121.4, 118.0, 117.9, 116.2, 115.9, 115.0, 55.8 ppm. IR (neat, cm−1): 3391, 3007, 1508, 1314, 1243, 1221, 1027, 814, 772, 591. Anal. Calcd. for C13H12FNO: C, 71.87; H, 5.57. Found: C, 71.89; H, 5.62.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c8234776362b482d979278fd19197e2e
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

Loading…