Trifluoromethanesulfonic anhydride → 6-(4-Fluorophenyl)-2-naphthyl trifluoromethanesulfonate

HRID 735303Notes

Reaction equation

FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH:29]=[C:28](O)[CH:27]=[CH:26]3)=[CH:19][CH:18]=1>ClCCl.N1C=CC=CC=1>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23]([C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)[CH:24]=2)[CH:29]=1)(=[O:8])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoromethanesulfonic anhydride (1.3 mL, 7.74 mmol) was added over 5 minutes to a stirred solution of 6-(4-fluorophenyl)-2-naphthol (Step 1, 1.75 g, 7.35 mmol) in dichloromethane (25 mL) and pyridine (15 mL) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour then allowed to warm to room temperature. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give 6-(4-fluorophenyl)-2-naphthyl trifluoromethanesulfonate (2.34 g, 86%). 1H NMR (500 MHz, CDCl3) δ 8.03 (1H, s), 7.96 (2H, dd, J=9.1, 13.1 Hz), 7.81-7.77 (2H, m), 7.67-7.65 (2H, m), 7.41 (1H, dd, J=2.4, 9.0 Hz), 7.21-7.17 (2H, m).

Workup

temperatureto warm to room temperature
customThe solvent was removed in vacuo
customthe residue partitioned between ethyl acetate and water
washThe combined organic layers were washed with water and brine
dry with materialdried over MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-23fc0cbb4c23484eb9d1a08953d0af75
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592456B2

Reaction notes

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