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Benzene, 1-bromo-3-(trifluoromethyl)- → 2,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-ol

HRID 26289
Notes
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Reaction equation

HRID 26289 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:13][C:14]1([CH3:26])[CH2:23][C:22](=O)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1.[Cl-].[NH4+]>CCOCC>[CH3:13][C:14]1([CH3:26])[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

Product 1

HCID 120717572,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-olYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
3×

Procedure

3-Bromobenzotrifluoride (61 g) in dry ether (100 ml was added to magnesium (6.6 g) in ether (50 ml). 2,2-Dimethylchroman-4-one-7-ol (17.4 g) suspended in ether (500 ml) was added and the mixture refluxed for 16 hourss. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The combined ether layers were washed with 2 N HCl (2×100 ml) and dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound (25 g), m.p. 102°-106° C.

Workup

  1. additionwas added
  2. temperaturethe mixture refluxed for 16 hourss
  3. extractionextracted with ether
  4. washThe combined ether layers were washed with 2 N HCl (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-58a9c8d907364fbda18f7e7cdb4bebbe
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04148909

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes