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

HRID 216248

반응식

HRID 216248 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4f115a5c2ffd4783a3a9e5939fa2c143
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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