Water → 5-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid

HRID 216248

反応式

HRID 216248 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].[Br:13]Br.O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:13][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]=2[CH:9]=1

参加物

6

反応物 4

HCID 962WaterHCID 24408BromineHCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acidHCID 23665763Sodium Bisulfite

生成物 1

HCID 186242435-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid収率 107.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 2,3-dihydro-benzofuran-2-carboxylic acid (510 mg, 3.11 mmol) in glacial acetic acid (4 mL) is added bromine (497 mg, 3.11 mmol) dropwise. After 16 hours, the reaction is quenched with water (100 mL) and sodium bisulfite (1 g, 9.6 mmol) and extracted twice with EtOAc (100 mL). The extracts are concentrated in vacuo and dried under high vacuum to afford 5-bromo-2,3-dihydro-benzofuran-2-carboxylic acid (811 mg) as a solid. MS: 241 (M+H), 1H NMR [300 MHz, (CD3)2SO]: δ 13.05 (1H, s); 7.4 (1H, s); 7.25 (1H, d); 6.8 (1H, m); 5.25 (1H, q), 3.55 (1H, dd); 3.25 (1H, m).

後処理

  1. extractionextracted twice with EtOAc (100 mL)
  2. concentrationThe extracts are concentrated in vacuo
  3. customdried under high vacuum

出典と根拠

ORDレコード
ord-4f115a5c2ffd4783a3a9e5939fa2c143
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

関連ノート

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