Potassium Hydroxide → HCID 22093448, compound

HRID 457964Notes

Reaction equation

HRID 457964 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 Na2SO4, 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, 1 H), 8.97 (t, J=5.4 Hz, 1 H), 7.75 (dd, J1=8.4 Hz, J2=0.3 Hz, 1 H), 7.48 (d, J=9.6 Hz, 1 H), 7.37–7.26 (m, 2 H), 6.46 (dd, J1=8.7 Hz, J2=2.1 Hz, 1 H), 6.40 (s, 1 H), 4.77 (s, 2 H), 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. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cf1f24eda4a246518ff72f0594281ec2
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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