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

HRID 2110776Notes

Reaction equation

HRID 2110776 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-edc336e77e8f40fdaa05a8499d212d61
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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