Potassium Hydroxide → HCID 9957700, compound

HRID 857153Notes

Reaction equation

HRID 857153 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:14]=[CH:15][C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:18][C:17]=3[CH:27]=2)=[C:7]([Br:28])[CH:6]=1.[OH-].[K+]>C(O)C>[Br:28][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:29])=[O:2])[CH:10]=[C:9]([Br:11])[C:8]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:18][C:17]=2[CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21867230HCID 21867230, compound

Product 1

HCID 9957700HCID 9957700, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl[3,5-dibromo-4-(2-phenyl-5-benzofuranyloxy)phenyl]acetate (200 mg) was diluted in ethanol (2 mL) and treated with an aqueous saturated solution of potassium hydroxide (0.5 mL). The reaction mixture was refluxed for 1.5 hours. The reaction mixture was concentrated, diluted with chloroform and washed with an aqueous solution of hydrochloric acid (1 N). The organic phase was dried over magnesium sulphate, filtered and concentrated. This gave 0.13 g (70%) of 3,5-dibromo-4-(2-phenyl-5-benzofuranyloxy)-phenylacetic acid as a beige solid mass. 1H-NMR (300 MHz, DMSO-d6): δ 12.5 (br s, 1H), 7.86 (d, J=7.2 Hz, 2H), 7.34 (s, 2H), 7.61 (d, J=8.4 Hz, 1H), 7.50 (t, J=5.1 Hz, 3H), 7.42 (d, J=7.1, 1H), 7.35 (s, 1H), 6.87 (s, 1H), 3.70 (s, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with chloroform
  4. washwashed with an aqueous solution of hydrochloric acid (1 N)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3c52d5f650e2430098e23586acc92ea6
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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