Trifluoroacetic acid → 4-(Adamantan-2-yl)-3-chlorobenzoic acid

HRID 1849789Notes

Reaction equation

HRID 1849789 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[C:15]1(O)[CH:22]2[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:24][CH:16]1[CH2:17]3)[CH2:21]2)[C:5]([O:7]C(C)(C)C)=[O:6].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:16]12[CH2:24][CH:20]3[CH2:19][CH:18]([CH2:23][CH:22]([CH2:21]3)[CH:15]1[C:14]1[CH:13]=[CH:12][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[Cl:1])[CH2:17]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86703670Tert-butyl 3-chloro-4-(2-hydroxyadamantan-2-yl)benzoate

Product 1

HCID 867036714-(Adamantan-2-yl)-3-chlorobenzoic acidYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-chloro-4-(2-hydroxyadamantan-2-yl)benzoate (0.581 g, 1.60 mmol) in dichloromethane (50 mL) was added triethylsilane (5 mL) and trifluoroacetic acid (5 mL). The reaction mixture was stirred at ambient temperature for 20 hours and the reaction solution was concentrated in vacuo to dryness. The residue was triturated with hexanes (15 mL) to afford the title compound (0.27 g, 57%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.06 (d, J=1.6 Hz, 1H), 7.94 (dd, J=1.6, 8.2 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 3.33 (s, 1H), 2.33 (br s, 2H), 1.98-1.92 (m, 8H), 1.78 (s, 2H), 1.70-1.66 (m, 2H) (OH not observed); MS (ES−) m/z 289.3, 291.3 (M−1).

Workup

  1. concentrationthe reaction solution was concentrated in vacuo to dryness
  2. customThe residue was triturated with hexanes (15 mL)

Sources & evidence

ORD record
ord-e1b073e67e454c5e80aa92ca08011edc
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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