Bromine → 3-Bromo-6-methoxy-2-methylbenzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5]([OH:7])=[O:6].[Br:13]Br>ClC1C=CC=CC=1>[Br:13][C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([C:8]=1[CH3:12])[C:5]([OH:7])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
700 g (4.212 mol) of 2-methoxy-6-methylbenzoic acid (IV′) were suspended in 2343.5 g of chlorobenzene, and 707.2 g (4.423 mol) of elemental bromine were subsequently added dropwise within 3 h at a constant internal temperature of 15° C. Afterwards, the mixture was stirred at 35° C. for 2 h. Subsequently, 628.7 g of chlorobenzene were distilled off at an internal temperature of 77-82° C. and 200 mbar, and the excess bromine and HBr were likewise removed from the reaction vessel. After analysis of the bromine content, the brominous chlorobenzene distillate could be reused in the next batch without any discharge. The amount of bromine to be used there could be correspondingly reduced.
Workup
- distillationSubsequently, 628.7 g of chlorobenzene were distilled off at an internal temperature of 77-82° C. and 200 mbar
- customthe excess bromine and HBr were likewise removed from the reaction vessel
Sources & evidence
- ORD record
- ord-72c5285d211e43078cbe4a468b908100
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253323B2
Reaction notes
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