p-Toluenesulfonic acid → 4-Bromo-2-[(2,4-difluorobenzylidene)amino]-5-fluorophenol

HRID 1668353Notes

Reaction equation

HRID 1668353 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[OH:10].[F:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([OH:10])=[C:2]([N:1]=[CH:14][C:13]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=2[F:11])[CH:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 737702,4-DifluorobenzaldehydeHCID 383722992-Amino-4-bromo-5-fluorophenol

Product 1

HCID 673576654-Bromo-2-[(2,4-difluorobenzylidene)amino]-5-fluorophenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-amino-4-bromo-5-fluorophenol (10.1 g, 49 mmol), 2,4-difluorobenzaldehyde (5.36 mL, 49 mmol) and p-toluenesulfonic acid (100 mg, 0.52 mmol) in toluene (250 mL) was heated to reflux in a Dean-Stark apparatus for 0.5 h and then allowed to cool to ambient temperature. After adding triethylamine (1 mL) the reaction mixture was concentrated under reduced pressure to give the crude compound which was used without further purification. (16.1 g, 99%). 1H-NMR (400 MHz, CDCl3) 6.83 (d, J=10.2, 1H), 6.93 (m, 1H), 7.01 (m, 1H), 7.49 (d, J=7.6, 1H), 8.13 (m, 1H), 8.85 (s, 1H).

Workup

  1. temperatureto reflux in a Dean-Stark apparatus for 0.5 h
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-58a2bf9c035d484e916acf81cb8953cd
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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