4-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole → 4-Bromomethyl-2-(4-methoxymethoxyphenyl)benzoxazole

HRID 2213998Notes

Reaction equation

HRID 2213998 reaction equation
[Br:1][CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16](OC)[CH:15]=[CH:14][C:13]=3OCOC)[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:24][O:25][CH2:26][O:27]C1C=CC(C2OC3C=CC=C(C)C=3N=2)=CC=1>>[Br:1][CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:27][CH2:26][O:25][CH3:24])=[CH:16][CH:17]=3)[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 219593264-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazoleHCID 219593302-(4-Methoxymethoxyphenyl)-4-methylbenzoxazole

Product 1

HCID 219593284-Bromomethyl-2-(4-methoxymethoxyphenyl)benzoxazole

Procedure

4-bromomethyl-2-(4-methoxymethoxyphenyl)benzoxazole (F15) was prepared in a similar manner for the preparation of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) by using 2-(4-methoxymethoxyphenyl)-4-methylbenzoxazole (F11) (4.04 g, 15 mmol) instead of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F8) in 80% (4.16 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-7cdba657aa4e469cb67554cff2b048e6
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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