Hydrochloric Acid → 2-(Aminomethyl)-3,5-dichlorobenzenemethanol

HRID 1051938Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[C:14]#[N:15])(=O)C.CO.Cl>C1COCC1.O.CCOC(C)=O>[NH2:15][CH2:14][C:7]1[C:8]([Cl:13])=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=1[CH2:5][OH:4]

Participants

Conditions

Temperature: 75 °C

Procedure

To a soln. of 3,5-dichloro-2-cyanobenzyl acetate (11.7 mmol) in 50 mL THF was added a soln. of BH3 (50 mmol, 1M in THF). The reaction mixture was heated to 75° C. for 7 h and then cooled to 0° C. Water was added followed by MeOH and the mixture was conc. The residue was taken up in water and EtOAc, acidified with 1N HCl solution and extracted with DCM. The aq. phase was then basified with 1M NaOH soln. and extracted with DCM. The comb. org. layers were dried over MgSO4 and conc. in vacuo. Purification with CC (0-10% MeOH/DCM; 1% Et3N) gives the desired compound as pinkish solid.

Workup

temperaturecooled to 0° C
extractionextracted with DCM
extractionand extracted with DCM
dry with materiallayers were dried over MgSO4 and conc. in vacuo
customPurification with CC (0-10% MeOH/DCM; 1% Et3N)

Sources & evidence

ORD record: ord-918427e2baa64379b6073545155038d0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388197B2

Reaction notes

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