Trifluoroacetic acid → HCID 22731330, compound

HRID 2085583Notes

Reaction equation

HRID 2085583 reaction equation
[C:1]([C:9]1[C:17]2[O:16][CH2:15][C:14]([CH3:19])([CH3:18])[C:13]=2[CH:12]=[C:11]([Br:20])[CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH2:1]([C:9]1[C:17]2[O:16][CH2:15][C:14]([CH3:18])([CH3:19])[C:13]=2[CH:12]=[C:11]([Br:20])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22731287HCID 22731287, compound2×

Product 1

HCID 22731330HCID 22731330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure J and using 7-benzoyl-5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran (Intermediate 38, 2.15 g, 6.53 mmol), anhydrous dichloromethane (10 mL), trifluoroacetic acid (4.12 mL, 53.5 mmol) and triethyl silane (8.4 mL, 52 mmol) followed by flash column chromatography, the title compound was obtained (1.57 g, 76%). 1H NMR (300 MHz, CDCl3): δ 7.23-7.14 (m, 5H), 7.02 (d, 1H, J=1.9 Hz), 6.97 (d, 1H, J=1.9 Hz), 4.17 (s, 2H), 3.85 (s, 2H), 1.36 (s, 6H).

Sources & evidence

ORD record
ord-07b4308c68884b0986e73797aa41c9ea
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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