Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 21459095, compound

HRID 725391Notes

Reaction equation

HRID 725391 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:22]=[O:23]>S(=O)(=O)(O)O>[CH2:28]([O:27][C:26]1[CH:25]=[CH:24][C:21]([CH:22]([OH:23])[C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[CH:20][C:19]=1[O:18][CH3:17])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 21459095HCID 21459095, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

92 ml of n-butyl lithium solution (1.6M in hexane) are added dropwise at -70° within 20 minutes to 33.0 g of 4-bromobenzotrifluoride (dissolved in 150 ml of tetrahydrofuran). After stirring at -70° for 45 minutes, 36 g of 3-methoxy-4-benzyloxybenzaldehyde (dissolved in 100 ml of tetrahydrofuran) are added dropwise thereto at between -70° and -60°. The reaction mixture is stirred at -70° for 2 hours and at 0° for 1 hour, poured into a mixture of ice and 100 ml of 2N sulfuric acid and extracted twice with 500 ml of ether. The combined ether phases are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. There is obtained 4-(benzyloxy)-3-methoxy-4'-(trifluoromethyl)benzhydrol which can be used directly in the subsequent reaction step.

Workup

  1. customat between -70° and -60°
  2. stirringThe reaction mixture is stirred at -70° for 2 hours and at 0° for 1 hour
  3. extractionextracted twice with 500 ml of ether
  4. washThe combined ether phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0a291e31404d4958b98d6f84af484579
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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