Thionyl bromide → HCID 18761815、化合物

HRID 432046ノート

反応式

HRID 432046 の反応式
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(Br)([Br:21])=O>C1(C)C=CC=CC=1>[Br:21][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2

参加物

4

反応物 2

HCID 68176Thionyl bromideHCID 99211661-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol

生成物 1

HCID 18761815HCID 18761815、化合物収率 103.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension of 5-hydroxymethyl-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (2 g, 8.2 mmol) in toluene (20 mL) was heated until the solid dissolved. Heating was then stopped. Thionyl bromide (2.2 g, 10.6 mmol) was added, and the mixture was stirred for 1 h. Silica (25 g) was added, and the mixture was filtered, and the residue was washed with a 1:1 v/v solution of ethyl acetate and heptane. The filtrate was evaporated to give the title compound as a red-orange oil (2.6 g, 90%). 1H NMR (d6-DMSO): δ 4.72 (s, 2H), 5.11 (d, 1H), 5.28 (d, 1H), 6.17 (s, 1H), 7.04 (d, 1H), 7.17 (t, 2H), 7.33 (d, 1H), 7.38 (dd, 2H), 7.45 (s, 1H).

後処理

  1. temperaturewas heated until the solid
  2. dissolutiondissolved
  3. temperatureHeating
  4. additionSilica (25 g) was added
  5. filtrationthe mixture was filtered
  6. washthe residue was washed with a 1:1 v/v solution of ethyl acetate and heptane
  7. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-a24a41cb4b4b43679ed8ced00790292f
出典データセット
uspto-grants-2003_12
特許番号
US06660873B2

反応ノート

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