2-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole → 4-Bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole

HRID 2213996Notes

Reaction equation

HRID 2213996 reaction equation
[Br:1][CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=3[O:20][CH2:21][O:22][CH3:23])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:24][O:25]C1C(OC)=CC(C2OC3C=CC=C(C)C=3N=2)=C(OCOC)C=1>>[Br:1][CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:25][CH3:24])=[CH:14][C:13]=3[O:20][CH2:21][O:22][CH3:23])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 219593182-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazoleHCID 219593264-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole

Product 1

HCID 219593354-Bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole

Procedure

4-bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole (F13) was prepared in a similar manner for the preparation of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) by using 2-(4,5-dimethoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F9) (1.39 g, 4.23 mmol) instead of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F8) in 66% (1.14 g): 1H-NMR (500 MHz, CDCl3) δ3.60 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 4.96 (s, 2H), 5.31 (s, 2H), 6.85 (s, 1H), 7.30 (t, 1H, J=8.0 Hz), 7.40 (d, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.66 (s, 1H).

Sources & evidence

ORD record
ord-8ae9347fc5534ae2bd396ddd29b1f58c
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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