o-(Trifluoromethyl)benzaldehyde → HCID 19825712, compound

HRID 2249167Notes

Reaction equation

HRID 2249167 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH:6]=[CH:5]2.C([Li])(C)(C)C.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>>[CH3:12][C:7]1([CH3:13])[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:23]([OH:24])[C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[C:20]([F:19])([F:29])[F:30])[CH:3]=2)[O:8]1

Participants

4

Reactant 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 117705336-Bromo-2,2-dimethyl-2H-chromeneHCID 178418306HCID 178418306, compound

Product 1

HCID 19825712HCID 19825712, compound

Procedure

6-Bromo-2,2-dimethyl-2H-chromene is metallated at -78° C. using 2 equivalents of tert.-butyllithium and subsequently reacted with 2-trifluoromethylbenzaldehyde to give 2,2-dimethyl-6-(2-trifluoromethyl-hydroxybenzyl)-2H-chromene which is produced as an oil.

Workup

  1. customis metallated at -78° C.

Sources & evidence

ORD record
ord-b4a7b1eff10248de8c7c1eedf1a17de9
Source dataset
uspto-grants-1991_08
Patent number
US05043344

Reaction notes

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