Hydrogen Bromide → (R)-Methyl 2-bromo-2-phenylacetate

HRID 1750980ノート

反応式

HRID 1750980 の反応式
N[C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[BrH:13].N([O-])=O.[Na+]>O>[Br:13][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4]

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 1201451Methyl phenylglycinate, L-HCID 23668193Sodium Nitrite

生成物 1

HCID 6993590(R)-Methyl 2-bromo-2-phenylacetate収率 40.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

(S)-methyl 2-amino-2-phenylacetate (5 g, 24.8 mmol, 1 equiv) was dwassolved in a mixture of 48% hydrogen bromide (13 ml, 198 mmol, 8 equiv) and water (19 ml). An aqueous solution of sodium nitrite (5.48 g, 79.36 mmol, 3.2 equiv) was added slowly and the mixture stirred at 0° C. for 1.5 h. The reaction was degassed in vacuo and extracted with ether. The organic layer was further washed with water and brine, dried over MgSO4, and concentrated in vacuo. The resulting residue was purified using the Biotage flash chromatography system (SNAP 100 g cartridge, Rf=0.5, gradient—1%-10% ethyl acetate in hexanes) to afford the (R)-methyl 2-bromo-2-phenylacetate as a light yellow oil (2.3 g, 40% yield); 1H NMR (400 MHz, DMSO-d6): δ 3.72 (s, 3H); 5.95 (s, 1H); 7.36-7.42 (m, 3H); 7.54 (d, 2H, J=1.6 Hz); 7.56 (d, 1H, J=2 Hz); MS for C9H9BrO2 m/z 229.98 (M+H)+.

後処理

  1. customThe reaction was degassed in vacuo
  2. extractionextracted with ether
  3. washThe organic layer was further washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

出典と根拠

ORDレコード
ord-72810b0b6bce4894a9337d2f41441f8a
出典データセット
uspto-grants-2015_10
特許番号
US09156840B2

反応ノート

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