Carbon tetrabromide → 4-(2-Bromoethoxy)-2-methoxyphenyl acetate

HRID 1805908

반응식

HRID 1805908 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32]O)=[CH:26][C:25]=1[O:34][CH3:35])(=[O:22])[CH3:21].C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[C:20]([O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][Br:37])=[CH:26][C:25]=1[O:34][CH3:35])(=[O:22])[CH3:21]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 673740454-(2-Hydroxyethoxy)-2-methoxyphenyl acetate

생성물 1

HCID 673760774-(2-Bromoethoxy)-2-methoxyphenyl acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of triphenylphosphine (0.123 mL, 0.530 mmol) in dry CH2Cl2 (1.3 mL) was added dropwise via cannula to a stirred solution of 4-(2-hydroxyethoxy)-2-methoxyphenyl acetate (100 mg, 0.442 mmol) and carbon tetrabromide (0.051 mL, 0.530 mmol) in dry CH2Cl2 (3.0 mL) at 0° C. under N2. After 5 h at 0° C., the reaction mixture was concentrated in vacuo and the residue obtained was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 1125 mL) to afford 4-(2-bromoethoxy)-2-methoxyphenyl acetate, as a colorless oil. Rf=0.78 (50% EtOAc/hexanes). LCMS calc.=289.1; found=288.8 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 6.93 (d, J=8.7 Hz, 1 H); 6.57 (d, J=2.8 Hz, 1 H); 6.42 (dd, J=8.7, 2.8 Hz, 1 H); 4.26 (t, J=6.2 Hz, 2 H); 3.80 (s, 3 H); 3.62 (t, J=6.2 Hz, 2 H); 2.29 (s, 3 H).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. customwas purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 1125 mL)

출처 및 근거

ORD 기록
ord-fd874ced9e0a423a8569ee5e3db32eb1
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354454B2

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