2-Bromoethyl methyl ether → 1-(2-Methoxyethoxy)-3-nitro-5-(trifluoromethyl)benzene

HRID 631392Notes

Reaction equation

HRID 631392 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].Br[CH2:16][CH2:17][O:18][CH3:19]>>[CH3:19][O:18][CH2:17][CH2:16][O:14][C:6]1[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

3

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Product 1

HCID 116946101-(2-Methoxyethoxy)-3-nitro-5-(trifluoromethyl)benzeneYield 46.2%

Procedure

3-nitro-5-(trifluoromethyl)phenol (770 mg, 3.72 mmol) and 1-bromo-2-methoxyethane (1.75 mL, 19 mmol) were reacted using the procedure described in Example 40A Step 3 to give 1-(2-methoxyethoxy)-3-nitro-5-(trifluoromethyl)benzene (456 mg, 1.72 mmol, 46%). 1H NMR (300 MHz, DMSO-d6) δ 8.05 (s, 1H), 8.02 (s, 1H), 7.80 (s, 1H), 4.36 (dd, 2H), 3.71 (dd, 2H), 3.31 (s, 3H); LC-MS (ESI) m/z 266 (M+H)+.

Sources & evidence

ORD record
ord-15390e8c01d648c3abbcfa1827a47915
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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