Hydrochloric Acid → 4-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acid

HRID 1849728Notes

Reaction equation

HRID 1849728 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:22]([I:23])=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[C:15]([F:24])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.O>[C:1]12([CH2:11][O:12][C:13]3[C:22]([I:23])=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:24])[CH:14]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 86703605Methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoate

Product 1

HCID 867036044-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoate (1.80 g, 4.05 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.85 g, 20.30 mmol) in water (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. After addition of 1 N hydrochloric acid (10 mL) and ethyl acetate (150 mL), the organic phase was separated, washed with 1 N hydrochloric acid (10 mL) and brine (10 mL); dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo yielded the title compound (1.75 g, quant) as an off-white solid, which was used without further purification: MS (ES−) m/z 429.1 (M−1).

Workup

  1. customthe organic phase was separated
  2. washwashed with 1 N hydrochloric acid (10 mL) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1a66f24dce4e4eed976ecb7569d96334
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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