Potassium Hydroxide → HCID 9823013, compound

HRID 611739Notes

Reaction equation

HRID 611739 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[S:17][C:16]=3[CH:15]=[CH:14][C:13]=2[Br:25])=[CH:8][CH:7]=1.[OH-].[K+]>O1CCCC1.CO>[Br:25][C:13]1[CH:14]=[CH:15][C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[C:20]=2[C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:26])=[O:2])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 9910377HCID 9910377, compound

Product 1

HCID 9823013HCID 9823013, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(2-bromo-dibenzothiophen-1-yl)-phenoxy]-acetic acid methyl ester (0.449 g, 1.05 mmol) in tetrahydrofuran (15 mL) and methanol (5 mL) was added an aqueous solution of potassium hydroxide (1N, 1.26 mL, 1.2 eq) dropwise at room temperature. After stirring 1 hour at room temperature the solvents were removed and the residue was disolved in water (50 mL) and the reaction mixture was acidified with 10% hydrochloric acid. After stirring 15 minutes the white solid was collected on a sintered glass funnel, washed with water and dried in vacuo at 58° C. overnight to give the title compound as a white solid (0.405 g, 93%); mp 209.5-210.5° C.; NMR (DMSO, d6): δ 13.06 (broad singlet), 8.02 (d, J=8 Hz, 1H), 8.01 (dd, J=8,1 Hz, 1H), 7.82 (d, J=8 Hz, 1H), 7.40 (ddd, J=8,7,1 Hz, 1H), 7.26-7.20 (m, 2H), 7.18=7.07 (m, 3H), 6.54 (d, J=8 Hz, 1H), 4.81 (s, 2H); MS [EI] M*+ m/z=412(98%), 414(100%), 1bromine isotope pattern detected, Anal. Calc. for C20H13BrO3S: C, 58.12, H, 3.17, N, 0.00. Found: C, 57.96, H, 2.95, N, 0.03.

Workup

  1. customwere removed
  2. stirringAfter stirring 15 minutes the white solid
  3. customwas collected on a sintered glass funnel
  4. washwashed with water
  5. customdried in vacuo at 58° C. overnight

Sources & evidence

ORD record
ord-02a51fd9fb4e4cf4a53e1785a15beddd
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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