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

HRID 2099170Notes

Reaction equation

HRID 2099170 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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 an 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).

Workup

  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)

Sources & evidence

ORD record
ord-1c4dd9f3e8bf4f36b8a4a1f09ae7de09
Source dataset
uspto-grants-2009_08
Patent number
US07569564B2

Reaction notes

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