1-Bromo-3-chloropropane → Ethyl 4-(3-chloropropoxy)-3-methoxybenzoate
Reaction equation
[C:1]([O:12][CH2:13][CH3:14])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+].[Br-].C([NH3+])CCC>>[Cl:19][CH2:18][CH2:17][CH2:16][O:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6]Participants
5
Procedure
WO 02/36587 describes a process for preparing a 5-alkoxy-4-halogenoalkoxy-2-nitrobenzoic acid compound from a 3-alkoxy-4-hydroxybenzoic acid compound. For example, ethyl vanillate (i.e., ethyl 4-hydroxy-3-methoxybenzoate) is reacted with 3-bromo-1-chloropropane in an aqueous potassium carbonate solution in the presence of N-butyl-ammonium bromide to produce ethyl 4-(3-chloropropoxy)-3-methoxybenzoate, and the ethyl 4-(3-chloropropoxy)-3-methoxybenzoate is reacted with 70% nitric acid in a mixture of dichloromethane and acetic acid, to give ethyl 4-chloropropoxy-3-methoxy-2-nitrobenzoate in 82% yield (based on the amount of ethyl vanillate).
Sources & evidence
- ORD record
- ord-2d443b9c4009440792a4e6c03db88f2a
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367824B2
Reaction notes
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