Chloromethyl Methyl Ether → 1-Bromo-2,3-bis(methoxymethyloxy)-4-methoxy-benzene

HRID 1836798

반응식

HRID 1836798 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([OH:10])[C:3]=1[OH:11].[O:12]1[CH2:16]CC[CH2:13]1.C(N(C(C)C)CC)(C)C.[CH3:26][O:27][CH2:28]Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:13][O:12][CH3:16])[C:3]=1[O:11][CH2:26][O:27][CH3:28]

참가 물질

6

반응물 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 37058743-Bromo-6-methoxybenzene-1,2-diol

생성물 1

HCID 105666271-Bromo-2,3-bis(methoxymethyloxy)-4-methoxy-benzene수율 91%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 1-bromo-2,3-dihydroxy-4-methoxy-benzene (5.0 g) and anhydrous tetrahydrofuran (20 mL) at 0° C. under argon was added diisopropylethylamine (8.0 mL). The solution was stirred for 15 min, methyloxymethyl chloride (3.5 mL) was added, and the reaction mixture stirred for 3 hours. The solution was poured into water (250 mL), extracted with dichloromethane and the solvent removed in vacuo to provide an orange oil. The oil was purified by flash column chromatography (hexane-ethyl acetate, 2:1) to yield a clear oil (6.4 g, 91%): EIMS m/z 308 (M+, 81Br), 306 (M+, 79Br), 232, 230, 45; IR (neat, cm−1) vmax 2963, 2836, 1221, 1159, 1084, 966; 1H NMR δ 7.25 (1H, d, J=9.0 Hz, H5), 6.61 (1H, d, J=9.0 Hz, H4), 5.20 (2H, s, OCH2), 5.13 (2H, s, OCH2), 3.84 (3H, s, OCH3), 3.66 (3H, s, OCH3), 3.59 (3H, s, OCH3); 13C—NMR (75.5 MHZ) δ 153.31, 148.24, 140.05, 127.49, 108.94, 108.73, 99.39, 98.73, 58.14, 57.46, 56.11. Anal. Calcd. For C11H15O5Br: C, 43.02; H, 4.92. Found: C, 42.86; H, 4.93.

후처리

  1. stirringthe reaction mixture stirred for 3 hours
  2. extractionextracted with dichloromethane
  3. customthe solvent removed in vacuo
  4. customto provide an orange oil
  5. customThe oil was purified by flash column chromatography (hexane-ethyl acetate, 2:1)

출처 및 근거

ORD 기록
ord-7754d388b453470ca553b337dfea0fb0
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777578B2

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