N,N-Dimethylbenzylamine → 3-Bromo-4-fluorobenzyl Alcohol
Reaction equation
C(OC(Cl)=O)C.[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][C:9]=1[Br:17].CN(C)CC1C=CC=CC=1>C(OCC)C>[F:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[Br:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
10.8 g of chloroformic acid ethyl ester were added dropwise to a solution of 20.8 g of 95% pure 4-fluoro-3-bromo-benzoic acid and 13.5 g of dimethylbenzylamine in 200 ml of diethyl ether at 0° C. Stirring was continued at 0° to 20° C. for 1 hour and the hydrochloride which had precipitated was then filtered off. After adding 0.1 g of triethylbenzylammonium bromide, a solution of 7.6 g of sodium borohydride in 50 ml of water was added dropwise to the filtrate at 20° C. The reaction mixture was subsequently stirred at 20° C. for 3 hours and was then acidified with dilute hydrochloric acid. The ether phase was separated off and washed once with 30 ml of saturated sodium bicarbonate solution. The ether phase was then concentrated. 17.3 g (93.4% of theory) of 4-fluoro-3-bromobenzyl alcohol were thus obtained in the form of a colorless oil.
Workup
- customthe hydrochloride which had precipitated
- filtrationwas then filtered off
- additionAfter adding 0.1 g of triethylbenzylammonium bromide
- additiona solution of 7.6 g of sodium borohydride in 50 ml of water was added dropwise to the filtrate at 20° C
- stirringThe reaction mixture was subsequently stirred at 20° C. for 3 hours
- customThe ether phase was separated off
- washwashed once with 30 ml of saturated sodium bicarbonate solution
- concentrationThe ether phase was then concentrated
Sources & evidence
- ORD record
- ord-ad5a734914934f80a7323c7d7fc3327c
- Source dataset
- uspto-grants-1983_05
- Patent number
- US04386035
Reaction notes
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