1-Bromo-4-(trifluoromethoxy)benzene → HCID 19436008, compound

HRID 1109958Notes

Reaction equation

HRID 1109958 reaction equation
[Mg].[CH2:2]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6].[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1>C1COCC1.Cl[Pd]Cl>[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:10]2[CH:9]=[CH:8][C:7]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:12][CH:11]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 27355991-Bromo-4-pentylbenzeneHCID 5462224Magnesium

Product 1

HCID 19436008HCID 19436008, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A Grignard compound is prepared from 1.2 g of magnesium, 50 ml of THF and 11.4 g of 4-pentyl-bromobenzene in 25 ml of THF. When the addition is complete, the mixture is refluxed for a further I hour and cooled to 10°, and 14 g of 4-trifluoromethoxy-bromobenzene in 25 ml of THF and 0.73 g of PdCl2 (dppf) are added. The cooling is removed, but the reaction mixture should not climb above 20°. The mixture is subsequently stirred at room temperature for 16 hours, poured into 100 ml of saturated NH4Cl solution a nd stirred for a further 15 minutes, and the organic phase is then worked up. After purification by crystallization, trifluoromethoxy-4-(4-pentylphenyl)benzene having C 67° I is obtained.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is refluxed for a further I hour
  3. temperaturecooled to 10°
  4. customThe cooling is removed
  5. customclimb above 20°
  6. additionpoured into 100 ml of saturated NH4Cl solution a nd
  7. stirringstirred for a further 15 minutes
  8. customAfter purification
  9. customby crystallization

Sources & evidence

ORD record
ord-5d44c00aad5c45dfbba41ca86c63df53
Source dataset
uspto-grants-1994_06
Patent number
US05324449

Reaction notes

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