Potassium Hydroxide → HCID 9913558, compound

HRID 611740Notes

Reaction equation

HRID 611740 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]([C:15]2[C:23]3[C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[S:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[C:11]([Br:28])[C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[K+]>CO>[Br:1][C:2]1[CH:14]=[C:13]([C:15]2[C:23]3[C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[S:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[C:11]([Br:28])[C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15870493HCID 15870493, compound

Product 1

HCID 9913558HCID 9913558, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [2,6-dibromo-4-(dibenzothiophen-1-yl)-phenoxy]-acetic acid, ethyl ester (0.324 g, 0.623 mmol) in tetrahyodrofuran (15 mL) and methanol (5 mL) was added an aqueous solution of potassium hydroxide (1N, 0.75 mL, 0.75 mmol, 1.2 eq) dropwise at room temperature. After stirring 2.5 hours at room temperature the solvents were removed and the residue was combined with water (50 mL) and was acidified with 10% aqueous hydrochloric acid. After stirring 0.5 hours the white solid was filtered. Trituration with petroleum ether and recrystallization from aqueous acetic acid with hot filtration gave a white solid which was dried in vacuo at 100° C. for 5 hours to provide the title compound as a white solid: (0.155 g, 51%); mp 212-213° C.; NMR (DMSO-d6): δ 13.19 (broad s, 1H), 8.11 (dd, J=8, 1 Hz, 1H), 8.04 (dm, 1H), 7.78 (s, 2H), 7.55 (dd, J=8, 7 Hz, 1H), 7.45 (ddd, J=8, 7, 1 Hz, 1H), 7.31 (dd, J=7 Hz, 1H), 7.27 (ddd, J=8, 7, 1 Hz, 1H), 7.10 (dm, 1H), 4.67 (s, 2H); MS (+FAB): [M+], 2 bromine isotope pattern, 490 (61%), 492 (100%), 494 (57%); Anal. Calc. for C20H12Br2O3S: C, 48.81, H, 2.46, N, 0.00. Found: C, 48.99, H, 2.24, N, 0.07.

Workup

  1. customwere removed
  2. stirringAfter stirring 0.5 hours the white solid
  3. filtrationwas filtered
  4. customTrituration with petroleum ether and recrystallization from aqueous acetic acid
  5. filtrationwith hot filtration
  6. customgave a white solid which
  7. customwas dried in vacuo at 100° C. for 5 hours

Sources & evidence

ORD record
ord-88d2169309b6454787e0ddb40494d2e3
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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