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

HRID 50660

反応式

HRID 50660 の反応式
[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]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 798582-Amino-5-bromobenzoic acidHCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0d885dd01d0a42a5a95c070c2d642ca4
出典データセット
uspto-grants-2004_03
特許番号
US06713478B2

関連ノート

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