Anisole → HCID 16107467, compound

HRID 556213Notes

Reaction equation

HRID 556213 reaction equation
COC1C=CC(C2[O:14][CH2:13][C:12]([CH2:30][O:31][C:32]([C:41]([F:44])([F:43])[F:42])([C:37]([F:40])([F:39])[F:38])[C:33]([F:36])([F:35])[F:34])([CH2:15][O:16][C:17]([C:26]([F:29])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])[CH2:11][O:10]2)=CC=1.C1(OC)C=CC=CC=1.[Al](Cl)(Cl)Cl>ClCCl>[F:19][C:18]([F:20])([F:21])[C:17]([C:26]([F:27])([F:28])[F:29])([C:22]([F:23])([F:24])[F:25])[O:16][CH2:15][C:12]([CH2:30][O:31][C:32]([C:33]([F:35])([F:36])[F:34])([C:37]([F:38])([F:39])[F:40])[C:41]([F:44])([F:43])[F:42])([CH2:11][OH:10])[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 24012Aluminum ChlorideHCID 16107459HCID 16107459, compound

Product 1

HCID 16107467HCID 16107467, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of compound 8 (33.1 g, 48.0 mmol) and anisole (20.7 g, 192.0 mmol) in dichloromethane (200 mL) at 0° C. was slowly added powdered aluminum chloride anhydrous (19.5 g, 144.0 mmol). After the addition, the reaction mixture was allowed to warm to room temperature and stirred for additional 30 minutes. The reaction mixture was quenched by slowly addition of 1N HCl (100 mL) and the resulted mixture was extracted with ether (100 mL, 3 times). The combined organic layer was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=8/1) to give compound 9 as a clear oil (27.4 g, 99%). 1H NMR (400 MHz, CD3OD) δ 3.63 (s, 4H), 4.14 (s, 4H); 19F NMR (376 MHz, CD3OD) δ −71.14 (s); 13C NMR (100.7 MHz, CD3OD) δ 47.8, 60.4, 69.1, 80.9 (m), 121.8 (q, J=292.6 Hz); MS (CI) m/z 573 (M++1, 100); HRMS (CI) Calcd for C13H11F18O4: 573.0374, Found: 573.0374.

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched by slowly addition of 1N HCl (100 mL)
  3. extractionthe resulted mixture was extracted with ether (100 mL, 3 times)
  4. concentrationThe combined organic layer was concentrated in vacuo
  5. customthe residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-602e091ee81d4fc6a0d7487430c0795e
Source dataset
uspto-grants-2011_11
Patent number
US08052961B2

Reaction notes

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