2-Chloroanisole → 3-Chloro-4-methoxybenzene-1-sulfonyl chloride

HRID 2273964ノート

反応式

HRID 2273964 の反応式
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14]>>[Cl:6][C:7]1[CH:12]=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

参加物

3

反応物 2

HCID 130112-ChloroanisoleHCID 24638Chlorosulfonic acid

生成物 1

HCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chloride収率 50%

反応条件

温度
55 °C

実験手順

Under N2 atmosphere, 41.25 mL chlorosulfonic acid was cooled in an ice bath, and under stirring 22.26 mL 2-chloroanisole was added dropwise. The mixture was heated to 55° C.; after 10 min. the heat source was removed and the mixture was stirred overnight at room temperature. The mixture was poured into ice water and extracted twice with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (PA/EA 9:1) to give 24.94 g (50%) of a beige oil. 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 7.08 (d, J=8.73 Hz, 1H), 7.94 (dd, J=9.03, 2.41 Hz, 1H), 8.06 (d, J=2.41 Hz, 1H).

後処理

  1. additionwas added dropwise
  2. customafter 10 min. the heat source was removed
  3. additionThe mixture was poured into ice water
  4. extractionextracted twice with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (PA/EA 9:1)

出典と根拠

ORDレコード
ord-bcf913be638a47cb9a360ae476250ba0
出典データセット
uspto-grants-2015_09
特許番号
US09126942B2

反応ノート

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