Water → 3,4-Dichlorobenzyl 2-(4-((3,4-dichlorobenzyl)oxy)phenyl)-2-hydroxyacetate

HRID 1427916노트

반응식

HRID 1427916 반응식
O.[OH:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24]Br.O>CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][O:5][C:4](=[O:6])[CH:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:24][C:23]2[CH:26]=[CH:27][C:28]([Cl:29])=[C:21]([Cl:20])[CH:22]=2)=[CH:9][CH:8]=1)[OH:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 126772902-Hydroxy-2-(4-hydroxyphenyl)acetic acid hydrate

생성물 1

HCID 669225903,4-Dichlorobenzyl 2-(4-((3,4-dichlorobenzyl)oxy)phenyl)-2-hydroxyacetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of hydroxy-(4-hydroxy-phenyl)-acetic acid monohydrate (10 g) in DMF (50 mL) was added K2CO3 (29.7 g) followed by 3,4-dichlorobenzyl bromide (16.1 mL). The mixture was stirred at room temperature for 3 h. The mixture was poured into water (250 mL) and extracted with EtOAc. The organic layer was washed with water 1N HCl, brine, dried over Na2SO4, and concentrated. The resulting solid was triturated with diethyl ether and filtered to provide [4-(3,4-dichloro-benzyloxy)-phenyl]-hydroxy-acetic acid 3,4-dichloro-benzyl ester as a white solid (9.4 g). 1H NMR (400 MHz, DMSO d6): 7.69 (d, 1H), 7.63 (d, 1H), 7.55 (d, 1H), 7.41 (m, 1H), 7.37 (d, 1H), 7.31 (m, 2H), 7.20 (m, 1H), 6.97 (m, 2H), 6.06 (d, 1H), 5.16 (d, 1H), 5.1 (m, 4H).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water 1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with diethyl ether
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-e221cd390b3740139a36123ef0c151a1
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933222B2

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