Diethyl Ether → Methyl 5-chloro-2-formylbenzoate

HRID 2092376노트

반응식

HRID 2092376 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13]([O-])([O-])=O.[K+].[K+].CI.CCOCC>CN(C=O)C>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH:11]=[O:12]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71762095-Chloro-2-formylbenzoic acid

생성물 1

HCID 58437623Methyl 5-chloro-2-formylbenzoate수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a heterogeneous mixture of 5-chloro-2-formyl-benzoic acid (1.0 g, 5.42 mmol) and K2CO3 (1.12 g, 8.13 mmol) in DMF (7 ml) was added MeI (0.41 ml, 6.5 mmol) at RT. The reaction mixture was stirred for 4 h then diluted into Et2O and washed with water (2×). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (700 mg, 3.52 mmol, 65%) as a light yellow solid, which was used without further purification. HPLC: AtRet=1.84 min; LC-MS: m/z 199.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 3.91 (s, 3H), 7.84-7.94 (m, 3H), 10.33 (s, 1H).

후처리

  1. washwashed with water (2×)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-9cb61c801d0542d3adb97f1dc38e9f0d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440693B2

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