Pivaloyl chloride → N-(2-Bromo-5-fluorophenyl)-2,2-dimethylpropanamide

HRID 132374ノート

反応式

HRID 132374 の反応式
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[NH2:16].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[NH:16][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

参加物

5

反応物 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 27733172-Bromo-5-fluoroaniline

生成物 1

HCID 59731998N-(2-Bromo-5-fluorophenyl)-2,2-dimethylpropanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trimethylacetyl chloride (4.2 mL, 34.1 mL) was fast dropwise added to a solution of 2-bromo-5-fluorobenzenamine (4.31 g, 22.7 mmol) in CH2Cl2 (50 mL) at room temperature, followed by the addition of DIEA (7.9 mL, 45.4 mmol). The resulting mixture was stirred at room temperature for 2 hrs, and then partitioned between HCl (1N, 200 mL) and EtOAc(250 mL). After separation, the organic phase was washed with brine (50 mL), dried on MgSO4, concentrated on rotary vacuum, and purified on flash chromatography eluting with 20˜40% EtOAc/hexanes (1200 mL) to afford the expected product, as a colorless oil (6.07 g, 98% yield); 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 9 H), 6.69 (ddd, J=8.81, 7.55, 3.02 Hz, 1 H), 7.45 (dd, J=8.81, 5.79 Hz, 1 H), 8.04 (s, 1 H), 8.28 (dd, J=11.08, 3.02 Hz, 1 H); Mass spec. 274.04 (MH+), Calc. for C11H13BrFNO 273.02.

後処理

  1. custompartitioned between HCl (1N, 200 mL) and EtOAc(250 mL)
  2. customAfter separation
  3. washthe organic phase was washed with brine (50 mL)
  4. customdried on MgSO4
  5. concentrationconcentrated on rotary vacuum
  6. custompurified on flash chromatography
  7. washeluting with 20˜40% EtOAc/hexanes (1200 mL)

出典と根拠

ORDレコード
ord-6eac0cac0b2943239349a0e0f20aabed
出典データセット
uspto-grants-2008_06
特許番号
US07384931B2

反応ノート

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