N-bromobutanimide → 2-Amino-3-bromo-5-chlorobenzaldehyde

HRID 913879Notes

Reaction equation

HRID 913879 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=[O:5].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(Cl)Cl>[NH2:1][C:2]1[C:9]([Br:11])=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27738982-Amino-5-chlorobenzaldehyde

Product 1

HCID 575461202-Amino-3-bromo-5-chlorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-chlorobenzaldehyde (2.1 g, 13.5 mmol) was dissolved in chloroform (20 mL) and treated with N-bromosuccinimide (2.6 g, 14.9 mmol). The reaction was stirred for 30 min at ambient temperature. The reaction was diluted with methylene chloride and washed with sodium thiosulfate (2×), 5% sodium bicarbonate (2×), water (2×), brine, dried over sodium sulfate, and concentrated to afford 3.0 g (95%) as a pale yellow powder. 1H-NMR (CDCl3, 500 MHz) δ 9.75 (s, 1H), 7.60 (d, J=2.4 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H). Mass spec.: 236.01 (MH)+.

Workup

  1. washwashed with sodium thiosulfate (2×), 5% sodium bicarbonate (2×), water (2×), brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford 3.0 g (95%) as a pale yellow powder

Sources & evidence

ORD record
ord-10628a0d96024bc0817995fda5905ccb
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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