1-Fluoro-4-(methylsulphonyl)benzene → [4-(4-Methanesulfonyl-phenoxy)-naphthalen-2-yl]-acetic acid

HRID 238607Notes

Reaction equation

HRID 238607 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.F[C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(O)(=O)C>[CH3:27][S:24]([C:21]1[CH:22]=[CH:23][C:18]([O:15][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:16])[CH:14]=2)=[CH:19][CH:20]=1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 59326576(4-Hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326475[4-(4-Methanesulfonyl-phenoxy)-naphthalen-2-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Starting with (4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (108 mg, 0.5 mmol) and 1-fluoro-4-methanesulfonyl-benzene (174 mg, 1.0 mmol), using a method analogous to the one described for example 1-1, the final two steps), 4-(4-methanesulfonyl-phenoxy)-naphthalen-2-yl]-acetic acid (65.8 mg, 37%) was obtained as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.89-7.94 (m, 4H), 7.71 (s, 1H), 7.54 (dt, J=8.08, 4.04 Hz, 1H), 7.48 (s, 2H), 7.14-7.19 (m, 3H), 3.80 (s, 2H), 3.11 (s, 3H); MS cald. for C19H16O5S 356, obsd. (ESI+) [(M+H)+] 357.

Sources & evidence

ORD record
ord-0a7f689621a54d03a311d17f3636e620
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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