Acetic Acid → Methyl 3-chloro-2-nitrobenzoate

HRID 132245

반응식

HRID 132245 반응식
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Si](C=[N+]=[N-])(C)(C)[CH3:15].CC(O)=O>CO.C(#N)C>[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 209023-Chloro-2-nitrobenzoic acidHCID 167693Trimethylsilyldiazomethane2회

생성물 1

HCID 12187125Methyl 3-chloro-2-nitrobenzoate수율 74.3%

시약·촉매·용매 1

HCID 21959252Acetonitrile methanol용매

실험 절차

To 3-chloro-2-nitrobenzoic acid (3.15 g, 15.6 mmol) in methanol/acetonitrile (20 mL/20 mL) was dropwise added TMSCHN2 (2N in hexanes, 11.7 mL, and 23.4 mmol) at 0° C. under N2 over 10 min until the yellow color persist. The mixture was continued stirring for 20 min, followed by dropwise addition of HOAc until the yellow color disappeared to kill excessive TMSCHN2. Partial of the solvent was removed on rotary vacuum, the product came out solution as a light yellow solid, which was filtered and washed with Et2O (2×2 mL) to afford the expected product as a white solid (2.5 g, 74% yield); 1H NMR (400 MHz, CDCl3) δ ppm 3.91 (s, 3 H), 7.51 (t, J=8.06 Hz, 1 H), 7.70 (dd, J=8.06, 1.26 Hz, 1 H), 7.97 (dd, J=7.81, 1.26 Hz, 1 H); Mass spec. 216.02 (MH+), Calc. for C8H6ClNO4 215.00.

후처리

  1. customat 0° C.
  2. customover 10 min
  3. customPartial of the solvent was removed on rotary vacuum
  4. filtrationwas filtered
  5. washwashed with Et2O (2×2 mL)

출처 및 근거

ORD 기록
ord-42ae182cd62e416c9cf1bbffc445fb92
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384930B2

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