Borane;tetrahydrofuran → HCID 14033036, compound

Temperature

0 °C

To a stirred solution/suspension of 3-chloro-5-methylbenzoic acid (800 mg, 4.69 mmol) in THF (5 ml) at 0° C. under nitrogen was added dropwise borane tetrahydrofuran complex (1 M in THF, 23.45 ml, 23.45 mmol) over 30 mins maintaining the temperature around 0° C. The reaction mixture was then allowed to warm to RT over 20 hrs. On cooling in an ice/water bath the reaction mixture was quenched dropwise with water and after a few minutes the THF was removed under reduced pressure. Water was added to the residue and on cooling a few drops of 1M HCl were added until effervescence ceased. The mixture was diluted with water and extracted into EtOAc, the organic portion dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-50% EtOAc in hexanes as eluent and azeotroping with toluene to afford the title product.

1. temperatureto warm to RT over 20 hrs
2. temperatureOn cooling in an ice/water bath the reaction mixture
3. customwas quenched dropwise with water and after a few minutes the THF
4. customwas removed under reduced pressure
5. additionWater was added to the residue
6. temperatureon cooling a few drops of 1M HCl
7. additionwere added until effervescence
8. additionThe mixture was diluted with water
9. extractionextracted into EtOAc
10. dry with materialthe organic portion dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customPurification
14. customazeotroping with toluene

ORD record

ord-97830858637e43c9862ab6fdd8532746

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2