Hydrochloric Acid → 2'-Bromoacetanilide

HRID 1749396Notes

Reaction equation

HRID 1749396 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[C:9](Cl)(=[O:11])[CH3:10].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 119922-Bromoaniline

Product 1

HCID 1364162'-BromoacetanilideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromophenylamine (1.0 equiv.) in DCM (0.2 M) was added acetyl chloride (1.5 M) at 0° C. The resulting mixture was stirred at this temperature overnight. 1 N hydrochloric acid (0.4 equiv.) was added to quench the reaction. The mixture was extracted with DCM and sodium bicarbonate and the combined organic layers were washed with brine, dried over sodium sulfate, concentrated and triturated from 16% ethyl acetate in petroleum ether to give the desired product (73% yield) as a white power. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.33-8.31 (m, 1H), 7.61 (br, 1H), 7.54-7.52 (m, 1H), 7.33-7.26 (m, 1H), 6.99-6.95 (m, 1H), 2.24 (s, 3H); MS (ESI) m/z 203.2 [M+H]+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with DCM and sodium bicarbonate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customtriturated from 16% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-2e9c74dc83474a61afcae678aabc8bd4
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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