2-(2,5-Dimethoxyphenyl)-4-methylbenzoxazole → 4-Bromomethyl-2-(2,5-dimethoxyphenyl)benzoxazole

HRID 2213997Notes

Reaction equation

HRID 2213997 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]OC)[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.COC1C=CC(OC)=CC=1C1OC2C=CC=C(C)C=2N=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])[CH:15]=[CH:14][C:13]=3[O:20][CH3:21])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 219593212-(2,5-Dimethoxyphenyl)-4-methylbenzoxazoleHCID 219593264-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole

Product 1

HCID 219593194-Bromomethyl-2-(2,5-dimethoxyphenyl)benzoxazole

Procedure

4-bromomethyl-2-(2,5-dimethoxyphenyl)benzoxazole (F14) was prepared in a similar manner for the preparation of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) by using 2-(2,5-dimethoxyphenyl)-4-methylbenzoxazole (F10) (4.55 g, 16.9 mmol) instead of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F8) in 56% (3.30 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-4ecd31894dca40d1a61aade1a4cc89d0
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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