Hydrochloric Acid → HCID 60167283, compound

HRID 2281864Notes

Reaction equation

HRID 2281864 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[Br:19])[CH:12]=[C:11]([C:20]([O:22]CC)=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O[Li].O.Cl>C1COCC1.O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[Br:19])[CH:12]=[C:11]([C:20]([OH:22])=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 60167282HCID 60167282, compound

Product 1

HCID 60167283HCID 60167283, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Ester 8 (2.29 g, 5.94 mmol) was dissolved in a 3:1:1 mixture of THF:CH3OH:H2O (0.1 M). LiOH—H2O was added and the reaction mixture was stirred at 25° C. for 24 h. Upon completion, the reaction mixture was acidified to pH 1 with the addition of 10% aqueous HCl. A precipitate formed during the acidification and it was collected by vacuum filtration. The remaining aqueous layer was then extracted with ethyl acetate (3×). The organic extracts were combined, dried over Na2SO4, and concentrated under reduced pressure. The filtered and extracted products were combined to give 9 (2.09 g, 100%) as a pale yellow solid. 1H NMR (DMSO-d6, 500 MHz) δ 8.23 (s, 1H), 8.10 (d, J=6.0 Hz, 1H), 7.91 (d, J=6.5 Hz, 1H), 7.61 (d, J=7.0 Hz, 2H), 7.55 (s, 1H), 7.43-7.39 (m, 3H), 7.33 (t, J=7.0 Hz, 1H), 5.35 (s, 2H). 13C NMR (DMSO-d6, 125 MHz) δ 166.7, 153.8, 136.2, 135.9, 135.0, 129.8, 128.8, 128.2, 127.8, 127.7, 127.5, 124.7, 123.8, 115.5, 107.0, 70.4. IR (film) νmax 3368, 2969, 1680 cm−1. ESI-TOF HRMS m/z 357.0125 (M+H+, C18H13BrO3 requires 357.0121).

Workup

  1. customA precipitate formed during the acidification and it
  2. filtrationwas collected by vacuum filtration
  3. extractionThe remaining aqueous layer was then extracted with ethyl acetate (3×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe filtered
  7. extractionextracted products

Sources & evidence

ORD record
ord-ddbd5dc671ea47e4a2d68f6e795b28ad
Source dataset
uspto-grants-2015_09
Patent number
US09139596B2

Reaction notes

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