Aluminium lithium hydride → (4-Amino-2-fluorophenyl)methanol

Temperature

2.5 °C

To a 250 ml three necked round bottom flask, methyl 4-amino-2-fluorobenzoate (2.75 g, 0.0162 mole) was added in anhydrous THF (60 ml) under nitrogen atmosphere and cooled to 0-5° C. After 15 minutes, 2.0 M solutions of LAH in THF (24.3 ml, 0.0487 mole) was added dropwise and stirred for 10 min. The reaction mixture was allowed to warm up to room temperature and stirred at same temperature for 1 hr. After completion of the reaction, the reaction mixture was cooled to 5° C. and quenched with sat. NH4Cl (25 ml) and diluted with water (100 ml) followed by extraction with ethyl acetate. The combined organics were washed with water, dried over sodium sulphate and evaporated to afford brown solid (crude) product which was purified using column purification by eluting the compound with 20% ethyl acetate in hexanes to yield 1.7 g of (4-amino-2-fluorophenyl)methanol.

1. temperatureto warm up to room temperature
2. stirringstirred at same temperature for 1 hr
3. customAfter completion of the reaction
4. temperaturethe reaction mixture was cooled to 5° C.
5. customquenched with sat. NH4Cl (25 ml)
6. additiondiluted with water (100 ml)
7. extractionfollowed by extraction with ethyl acetate
8. washThe combined organics were washed with water
9. dry with materialdried over sodium sulphate
10. customevaporated
11. customto afford brown solid (crude) product which
12. customwas purified
13. customcolumn purification
14. washby eluting the compound with 20% ethyl acetate in hexanes

ORD record

ord-298f46105ae543fa8acc3218651812d9

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187487B2