Oxalyl chloride → 3-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one

HRID 1992945Notes

Reaction equation

HRID 1992945 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[F:15][C:2]([F:1])([F:16])[CH:3]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:7])[CH2:4]1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 68541211HCID 68541211, compound

Product 1

HCID 137907913-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-oneYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,4,4-Trifluoro-3-(phenylmethyl)butanoic acid (177) (0.97 g, 4.18 mmol) was treated with oxalyl chloride followed by AlCl3 in CH2Cl2 to give 0.74 g (82%) of the title compound (178) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 2.60-2.75 (m, 1H), 2.85-3.00 (m, 2H), 3.05-3.25 (m, 2H), 7.30 (d, J=7.7 Hz, 1H), 7.37 (t, J=7.6 Hz, 1H), 7.50-7.57 (m, 1H), 8.05 (d, J=7.7 Hz, 1H). LCMS (ESI): m/z 215 (M−H)−.

Sources & evidence

ORD record
ord-872b74e5b75a43a8b740e3998f2e9066
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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