Sodium Carbonate → 2-(4'-Bromophenyl)aniline

HRID 1990060Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].I[C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[NH2:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Add 4-bromophenyl boronic acid (5.0 g, 24.82 mmol), tetrakis(triphenylphosphine)palladium (0) (0.717 g, 0.620 mmol) and 2 M Na2CO3 (10 mL) to a solution of 2-iodoaniline (4.5 g, 20.69 mmol) in toluene (2 mL):ethanol (20 mL), degas and heat at 80° C. under nitrogen. After 4 h, add water and extract with ethyl acetate. Combine the organic layers, dry over sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography (silica gel) eluting with ethyl acetate:hexane 1:12 to provide the title compound (3.53 g, 69%): Mass spectrum (m/e): 248 (M+1); 249 (M+2). 1HNMR (CDCl3), δ3.62 (s, 2H); 6.75-6.89 (m, 2 H); 7.08-7.18 (m, 2H); 7.21-7.40 (m, 2H); 7.55-7.63 (m, 2H):

Workup

customethanol (20 mL), degas
additionadd water
extractionextract with ethyl acetate
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customto give a residue
customPurify the residue by flash chromatography (silica gel)
washeluting with ethyl acetate:hexane 1:12

Sources & evidence

ORD record: ord-304c537a52ed4122a537d9c4a4ff4a69
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642361B2

Reaction notes

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