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

HRID 2300093ノート

反応式

HRID 2300093 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].CC[O:16][CH2:17][CH3:18].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:17]([OH:16])([CH3:18])[CH3:12]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 798582-Amino-5-bromobenzoic acidHCID 178477778HCID 178477778、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 brormide 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 column 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 column chromatography(hexane:ethyl acetate/3:2)

出典と根拠

ORDレコード
ord-ae1529e2adeb4a6c879c85bf0c50863c
出典データセット
uspto-grants-2002_12
特許番号
US06498154B1

反応ノート

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