Vanillin → 4-((2,4-BIS(TRIFLUOROMETHYL)BENZYL)OXY)-3-METHOXYBENZALDEHYDE

HRID 1012199Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]([F:16])([F:15])[F:14].[O:17]=[CH:18][C:19]1[CH:27]=[CH:26][C:24]([OH:25])=[C:21]([O:22][CH3:23])[CH:20]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[F:14][C:13]([F:16])([F:15])[C:4]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:3]=1[CH2:2][O:25][C:24]1[CH:26]=[CH:27][C:19]([CH:18]=[O:17])=[CH:20][C:21]=1[O:22][CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

To a flask was added 1-bromomethyl-2,4-bis-trifluoromethyl-benzene (2.27 g, 7.39 mmol), vanillin (1.12 g, 1 equiv), DMF (23 mL) and fine mesh K2CO3 (5.11 g, 37 mmol). The reaction slurry was stirred at 70° C. for 15 h. The reaction solution was diluted with EtOAc (120 mL), filtered through a Buchner funnel, washed with sat NH4Cl (50 mL×2), dried over Na2SO4, filtered, and concentrated. The crude material was chromatographed (SiO2, Hex/EtOAc: 100:0 to 70:30) to yield intermediate product (2.79 g, 86%). 1H NMR (400 MHz, CDCl3) δ 9.88 (s, 1H), 7.97 (d, J=8 Hz, 1H), 7.96 (s, 1H), 7.85 (d, J=8 Hz, 1H), 7.48 (s, 1H), 7.42 (d, J=8 Hz, 1H), 6.93 (d, J=8 Hz, 1H), 5.48 (s, 2H), 3.99 (s, 3H); MS (ESI) 379 (MH+).

Workup

filtrationfiltered through a Buchner funnel
washwashed with sat NH4Cl (50 mL×2)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was chromatographed (SiO2, Hex/EtOAc: 100:0 to 70:30)

Sources & evidence

ORD record: ord-8ce01345b1a64f3589f3b314349069de
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977489B2

Reaction notes

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