Potassium Hydroxide → HCID 22093448, compound

HRID 2229551Notes

Reaction equation

HRID 2229551 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])C.[OH-].[K+]>C(O)C.C(OCC)(=O)C>[OH:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:26])=[O:3])=[C:8]([C:14](=[O:25])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[F:24])[CH:9]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69451115HCID 69451115, compound

Product 1

HCID 22093448HCID 22093448, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [4-hydroxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (0.773 g, 1.83 mmol)in ethanol (10 mL, 0.18 M) was cooled to 0° C. and treated with aq KOH (5 mL, 1.25 M) and warmed to room temperature. The solution was acidified to pH 1-2, diluted with ethyl acetate and washed with sat'd aq NaCL. The organic layer was dried over Na2SO41 filtered and concentrated to give [4-hydroxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid as a white crystaline solid: mp 244 dec; 1H NMR (DMSO-d6, 300 MHz) δ 10.14 (br s, 1H), 8.97 (t, J=5.4 Hz, 1H), 7.75 (dd, J1=8.4 Hz, J2=0.3 Hz, 1H), 7.48 (d, J=9.6 Hz, 1H), 7.37-7.26 (m, 2H), 6.46 (dd, J1=8.7 Hz, J2=2.1 Hz, 1H), 6.40 (s, 1H), 4.77 (s, 2H), 4.47 (d, J=5.4 Hz, 2 Hz). Anal. calcd for C16H13BrFNO5: C, 48.26; H, 3.29; N, 3.52. Found C, 48.19; H, 3.52; N, 3.32.

Workup

  1. washwashed with sat'd aq NaCL
  2. customThe organic layer was dried over Na2SO41
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a7d8e53a83784c23bd375b4aa1f01692
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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