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

HRID 216248

Reaktionsgleichung

Reaktionsgleichung von HRID 216248
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 186242435-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acidAusbeute 107,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4f115a5c2ffd4783a3a9e5939fa2c143
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193183B2

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