4-(Trifluoromethyl)phenylboronic acid → 2-(3-Nitro-4-methoxyphenyl)-5-(4-trifluoromethylphenyl)benzoxazole

HRID 722503Notes

Reaction equation

HRID 722503 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18](Br)=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([O-:3])=[O:2].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[N+:1]([C:4]1[CH:5]=[C:6]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:27]4[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=4)=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 218843422-(3-Nitro-4-methoxyphenyl)-5-bromobenzoxazole

Product 1

HCID 218845742-(3-Nitro-4-methoxyphenyl)-5-(4-trifluoromethylphenyl)benzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-4-methoxyphenyl)-5-bromobenzoxazole (200 mg, 0.57 mmol) and 4-trifluoromethylphenylboronic acid (161 mg, 0.85 mmol) the subtitle compound was obtained (204 mg, 58%). 1H NMR (DMSO) δ 8.64(d, 1H), 8.46(dd, 1H), 8.16(d, 1H), 7.97(d, 2H), 7.92(d, 1H), 7.85–7.78(m, 3H), 7.63(d, 1H), 4.05(s, 3H).

Sources & evidence

ORD record
ord-b548cbcd629b4a1b8d604831f8e38378
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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