Acetic Acid → Methyl 3-chloro-2-nitrobenzoate

HRID 132245

反応式

HRID 132245 の反応式
[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]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 209023-Chloro-2-nitrobenzoic acidHCID 167693Trimethylsilyldiazomethane2 回

生成物 1

HCID 12187125Methyl 3-chloro-2-nitrobenzoate収率 74.3%

試薬・触媒・溶媒 1

HCID 21959252Acetonitrile methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-42ae182cd62e416c9cf1bbffc445fb92
出典データセット
uspto-grants-2008_06
特許番号
US07384930B2

関連ノート

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