Pivaloyl chloride → N-(2-Bromo-5-fluorophenyl)pivalamide

HRID 132374노트

반응식

HRID 132374 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 59731998N-(2-Bromo-5-fluorophenyl)pivalamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6eac0cac0b2943239349a0e0f20aabed
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

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