Dichloromethane → 5-Bromo-3,3-dimethyl-7-hexyl-2,3-dihydro-benzofuran

HRID 2085589Notes

Reaction equation

HRID 2085589 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.ClCCl>CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]2[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=2[CH:12]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 227312985-Bromo-3,3-dimethyl-7-hexanoyl-2,3-dihydrobenzofuran2×

Product 1

HCID 227312865-Bromo-3,3-dimethyl-7-hexyl-2,3-dihydro-benzofuran

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure J and using 5-bromo-3,3-dimethyl-7-hexanoyl-2,3-dihydrobenzofuran (Intermediate 52, 0.325 g, 1.0 mmol), trifluoroacetic acid (0.31 mL, 4 mmol), triethyl silane (0.64 mL, 4 mmol) and dichloromethane (5 mL) followed by flash column chromatography using 2% ethyl acetate in hexane as the eluent, the title compound was obtained (0.20 g, 64% for 2 steps).

Sources & evidence

ORD record
ord-910891ba1eae48548790226cc7216b27
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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