Hydrochloric Acid → 2-(2-Amino-5-bromophenyl)propan-2-ol

HRID 50660

Reaktionsgleichung

Reaktionsgleichung von HRID 50660
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1C(O)=O.[CH3:12][Mg]Br.CC[O:17][CH2:18][CH3:19].Cl.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:18]([OH:17])([CH3:19])[CH3:12]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 798582-Amino-5-bromobenzoic acidHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 120422752-(2-Amino-5-bromophenyl)propan-2-olAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-amino-5-bromobenzoic acid (10 g, 46 mmol) in dry THF (200 mL) was treated at −78° C. under nitrogen with a solution of methylmagnesium bromide in ether (3.0 M, 90 mL, 270 mmol). The reaction mixture was slowly warmed to ambient temperature, kept stirring for 48 hours under nitrogen and then poured into a cold 0.5 N aqueous hydrochloride solution (300 mL). The mixture was neutralized with aqueous 1 N sodium hydroxide solution and ethyl acetate (300 mL) was added. The organic layer was separated and aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine and dried (MgSO4). After removal of solvent in vacuo, the residue was purified by a silica gel flash chromatography (hexane:ethyl acetate/3:2) to give 2-(2-amino-5-bromophenyl)propan-2-ol as off-white solid (6 g, 57%): mp 62-63° C.; 1H-NMR (CDCl3) δ 7.19 (d, 1H, J=2.3 Hz), 7.12 (dd, 1H, J=8.4, 2.3 Hz), 6.51 (d, 1H, J=8.4 Hz), 4.70 (s, 2H), 1.82 (s, 1H), 1.65 (s, 6H).

Aufarbeitung

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customAfter removal of solvent in vacuo
  7. customthe residue was purified by a silica gel flash chromatography (hexane:ethyl acetate/3:2)

Quellen und Nachweise

ORD-Eintrag
ord-0d885dd01d0a42a5a95c070c2d642ca4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713478B2

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