Ethyl 4-(4-bromobenzoyl)benzoate → HCID 67341340, 화합물

HRID 1669281노트

반응식

HRID 1669281 반응식
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)([OH:19])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:9][CH:10]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 24722740Ethyl 4-(4-bromobenzoyl)benzoateHCID 178444609HCID 178444609, 화합물

생성물 1

HCID 67341340HCID 67341340, 화합물수율 19%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(4-Bromo-benzoyl)-benzoic acid ethyl ester (2.0 g, 6 mmol) in THF (20 mL) at 0° C. is added hexylmagnesium bromide (2M, 3.3 mL). After stirring at room temperature for 2 hours, it is quenched with saturated ammonium chloride, extracted with EtOAc. The organic is concentrated and purified by column chromatography to give 4-[1-(4-Bromo-phenyl)-1-hydroxy-heptyl]-benzoic acid ethyl ester (0.48 g, 19%), which is taken into methanol (2 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 3 h at room temperature. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1.1 mL), extracted with ethyl acetate. The organic layers are dried and concentrated giving to afford the titled compound (0.47 g).

후처리

  1. customit is quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic is concentrated
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-602d730a90ea482995583c873a041139
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989457B2

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