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

HRID 1427872Notes

Reaction equation

HRID 1427872 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:25]([CH:26]=[CH2:27])=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:15]([F:28])[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.FC(F)(F)C(O)=O>ClCCl>[C:1]12([CH2:11][O:12][C:13]3[C:25]([CH:26]=[CH2:27])=[CH:24][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:28])[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86702895Tert-butyl 4-(adamantan-1-ylmethoxy)-fluoro-5-vinylbenzoate

Product 1

HCID 867028964-(Adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoate (2.4 g, 6.2 mmol) in dichloromethane (10 mL), was added trifluoroacetic acid (10 ml). The reaction mixture was stirred at ambient temperature for 16 h and then concentrated in vacuo. The residue was triturated in hexanes (50 mL), the solid was filtered and dried to give the title compound as a light yellow solid (1.5 g, 73% in 2 steps): 1H NMR (300 MHz, DMSO-d6) δ 12.94 (br s, 1H), 7.92 (d, J=8.6 Hz, 1H), 6.96-6.81 (m, 2H), 5.84-5.78 (m, 1H), 5.32-5.28 (m, 1H), 3.62 (s, 2H), 3.34 (s, 3H), 1.95 (s, 3H), 1.70-1.60 (m, 12H); MS (ES+) m/z 331.2 (M+1); MS (ES−) m/z 329.4 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated in hexanes (50 mL)
  3. filtrationthe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-54b4e7c187fb4d0bbc6456b92a52e054
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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