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

HRID 216248Notes

Reaction equation

HRID 216248 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-4f115a5c2ffd4783a3a9e5939fa2c143
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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