4-(Bromomethyl)benzoic acid → Tert-butyl 4-(bromomethyl)benzoate
Reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1>COC(Cl)Cl>[C:3]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1)([CH3:11])([CH3:4])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
p-Bromomethyl benzoic acid (8.1 g) was refluxed with α,α dichloromethyl methyl ether (50 mL) for 1 h. The reaction mixture was evaporated to dryness, co-distilled with toluene twice and pumped under high vacuum. To the acid chloride redissolved in THF (100 mL) at −78° C. was added potassium tert-butoxide 1M in THF (30 mL) dropwise. Then temperature was raised to −20° C. and stirred for 1 h. The reaction mixture was quenched with NH4OAc and extracted with EtOAc. The organic phase was dried over Na2SO4 and evaporated to yield 50 g of tert-butyl-4-(bromomethyl)benzoate.
Workup
- customThe reaction mixture was evaporated to dryness, co-distilled with toluene twice
- dissolutionTo the acid chloride redissolved in THF (100 mL) at −78° C.
- additionwas added potassium tert-butoxide 1M in THF (30 mL) dropwise
- customThe reaction mixture was quenched with NH4OAc
- extractionextracted with EtOAc
- dry with materialThe organic phase was dried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-66b220a9766c4dba92513f67bc89861e
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06583126B2
Reaction notes
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