Hydrochloric Acid → Methyl 4-fluorobenzimidate hydrochloride

HRID 875028Notes

Reaction equation

HRID 875028 reaction equation
Cl.[F:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH3:11][OH:12].C(Cl)[Cl:14]>>[ClH:14].[F:2][C:3]1[CH:10]=[CH:9][C:6]([C:7](=[NH:8])[O:12][CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 145174-FluorobenzonitrileHCID 21226129Dichloromethane methanol

Product 1

HCID 14685563Methyl 4-fluorobenzimidate hydrochlorideYield 36%

Procedure

Dry HCl (g) was bubbled through a solution of 4-fluorobenzonitrile (5.0 g, 0.041 mol) in dry MeOH—CH2Cl2 (20 mL, 1:1 v/v) until saturation. The clear solution was kept at 0° C. for 2 days to crystallize methyl 4-fluorobenzimidate as hydrochloride salt, which was isolated by filtration (2.8 g, yield 36%). 1H NMR (400 MHz, DMSO-d6) δ 7.95-7.92 (m, 2H), 7.38 (br s, 1H), 7.29-7.25 (m, 2H), 3.06 (s, 3H). MS (ESI) m/z: Calculated for C8H8FNO: 153.06. found: 154.2 (M+H)+

Workup

  1. customto crystallize methyl 4-fluorobenzimidate as hydrochloride salt
  2. customwhich was isolated by filtration (2.8 g, yield 36%)

Sources & evidence

ORD record
ord-568217daa44e4efe97a0b4b5e08964e4
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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