Potassium Hydroxide → HCID 18687846, compound

HRID 1873221Notes

Reaction equation

HRID 1873221 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:34])[CH2:6][O:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([C:15]2[C:24]3[C:25]4[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=4[O:27][C:23]=3[C:22]([Br:32])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)=[CH:10][C:9]=1[Br:33]>C1COCC1.CO>[Br:14][C:13]1[CH:12]=[C:11]([C:15]2[C:24]3[C:25]4[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=4[O:27][C:23]=3[C:22]([Br:32])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:10]=[C:9]([Br:33])[C:8]=1[O:7][CH2:6][C:5]([OH:34])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54293587HCID 54293587, compound

Product 1

HCID 18687846HCID 18687846, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potasium hydroxide (1.0 M, 1.60 mL, 1.60 mmol) was added to a stirred solution of [2, 6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]furan-11-yl)-phenoxy]-acetic acid methyl ester (0.90 g, 1.45 mmol) in THF (9 mL) and methanol (5 mL). After 3 h, the solvent was removed, water was added and the reaction mixture was acidified with 10% HCl. After stirring overnight, the solid was filtered and washed with water, triturated with hexane and dried in vacuo at 100° C. to provide the title compound as a white solid (0.821 g, 94%): mp 250-252° C.: NMR (DMSO-d6); δ8.37 (d, J=8 Hz, 1 H), 7.90 (s, 2 H), 7.84 (d, J=8 Hz, 1 H), 7.70 (ddd, J=8, 6, 1 Hz, 1 H), 7.61 (ddd, J=8, 1, 1 Hz, 1 H)), 7.62-7.58 (m, 2 H), 7.31 (ddd, J=8, 7, 1 Hz, 1 H), 6.92 (ddd, J=8, 1,1 Hz, 1 H), 4.75 (s, 2 H); MS (EI): [M+], 3 bromine isotope pattern, 602 (40%), 604 (95%) 606 (100%) 608 (40%); Anal. Calc. for C24H13Br3O4: C, 47.64, H, 2.17, N, 0.00. Found: C, 47.33, H, 1.95, N, 0.04.

Workup

  1. customthe solvent was removed
  2. additionwater was added
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. customtriturated with hexane
  6. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-27740f6dee0246b1ae35d30bd9a1c859
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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