Allyl bromide → HCID 14085931, compound

HRID 603409Notes

Reaction equation

HRID 603409 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:12](Br)[CH:13]=[CH2:14].C([O-])([O-])=O.[Cs+].[Cs+]>O.CN(C=O)C>[CH2:14]([O:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)[CH:13]=[CH2:12]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 14085931HCID 14085931, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(Trifluoromethyl)phenol (1.50 g, 9.25 mmol), allyl bromide (14.55 g, 12.03 mmol), Cs2CO3 (3.62 g, 11.10 mmol), and water (15 drops) were combined in DMF (40 mL) and the mixture stirred for 12 h. The reaction mixture was then concentrated under reduced pressure, diluted with water, and extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure to give 0.96 g (51%) of the title compound as a light-yellow oil. 1H NMR (400 MHz, CDCl3): δ 4.59 (d, 2H), 5.32 (d, 1H), 5.43 (d, 1H), 6.05 (m, 1H), 6.97 (d, 2H), 7.53 (d, 2H).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with EtOAc (2×)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b45d94ab98214d0aba242b97401d37c7
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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