Hydrochloric Acid → Methyl 3-bromobenzimidate hydrochloride

HRID 70289Notes

Reaction equation

HRID 70289 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[ClH:10].[CH3:11][OH:12]>>[ClH:10].[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[NH:6])[O:12][CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 233813-Bromobenzonitrile

Product 1

HCID 14685566Methyl 3-bromobenzimidate hydrochloride

Procedure

A solution of m-bromobenzonitrile (1.82 g; 10 mmol) in MeOH (20 mL) at 0° C. was sparged with HCl gas for 30 min, the reaction flask was stoppered and aged in a refrigerator (ca. 5° C.) for 3 h. The mixture was sparged with N2 to remove excess HCl, concentrated in vacuo (2×PhMe chase) and dried under high vacuum ca. 45 min, affording the title compound as a colorless solid which was used directly for Step 2 below. LC/MS (method A) tR 0.81 min, m/z 214, 216 (M+H, Br isotopes).

Workup

  1. customThe mixture was sparged with N2
  2. customto remove excess HCl
  3. concentrationconcentrated in vacuo (2×PhMe chase)
  4. customdried under high vacuum ca. 45 min

Sources & evidence

ORD record
ord-116a652ec55f44e4a1bcf15c43d60ba5
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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