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

HRID 1836798

反応式

HRID 1836798 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7754d388b453470ca553b337dfea0fb0
出典データセット
uspto-grants-2004_08
特許番号
US06777578B2

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