Sulfuric Acid → 4-(bromomethyl)benzamide

HRID 508899Notes

Reaction equation

HRID 508899 reaction equation
[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[OH:11]S(O)(=O)=O>>[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]([NH2:8])=[O:11])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 5842164-(bromomethyl)benzamide

Procedure

Stirred the solution of 4-(bromomethyl)benzonitrile (1.5 g) in cocn.H2SO4 at 100° C. for 3-4 h. After completion of the reaction, the reaction mass was quenched in ice and filtered to afford 0.900 of desired product. 1H NMR (400 MHz, DMSO d6): δ 4.71 (s, 2H), 7.26 (br s, 1H), 7.49 (d, J=7.8 Hz, 2H), 7.82 (d, J=7.8 Hz, 2H), 7.89 (br s, 1H); MS (m/z): 214.36 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mass was quenched in ice
  3. filtrationfiltered

Sources & evidence

ORD record
ord-dcf669e0b4164171b910d1be905ecaac
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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