4-(Adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acid → 4-(Adamantan-1-ylmethoxy)-5-ethyl-2-fluorobenzoic acid

HRID 1849553Notes

Reaction equation

HRID 1849553 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH:22]=[CH2:23])=[CH:20][C:16]([C:17]([OH:19])=[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.[H][H]>[Pd].C(OCC)(=O)C>[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH2:22][CH3:23])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:24])[CH:14]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 2

HCID 867028964-(Adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 867028974-(Adamantan-1-ylmethoxy)-5-ethyl-2-fluorobenzoic acidYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acid (1.00 g, 3.03 mmol) and 10% palladium on activated carbon (0.10 g) in ethyl acetate (150 mL) was fitted with a hydrogen balloon. The reaction mixture was stirred at ambient temperature for 42 h. The mixture was filtered through a pad of diatomaceous earth, and washed with ethyl acetate (50 mL). The filtrate was concentrated in vacuo, the residue was recrystallized from ethyl acetate and hexanes to afford the title compound as an off-white solid (0.75 g, 74%): 1H NMR (300 MHz, DMSO-d6) δ 12.80 (br s, 1H), 7.63 (d, J=8.6 Hz, 1H), 6.87 (d, J=13.2 Hz, 1H), 3.61 (s, 2H), 5.57 (d, J=7.5 Hz, 2H), 1.99 (s, 3H), 1.75-1.63 (m, 12H), 1.14 (t, J=7.5 Hz, 3H); MS (ES+) m/z 333.2 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washwashed with ethyl acetate (50 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-8ee05e4f71294a02ac0d1f13ba17e388
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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