Benzyl Bromide → 2-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran

HRID 582604Notes

Reaction equation

HRID 582604 reaction equation
[OH:1][CH:2]([C:17]([F:20])([F:19])[F:18])[CH2:3][CH:4]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:6]=2[O:5]1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:22]1([CH2:21][O:1][CH:2]([C:17]([F:20])([F:18])[F:19])[CH2:3][CH:4]2[CH2:9][CH2:8][C:7]3[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:6]=3[O:5]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 153456662-(2-Hydroxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran

Product 1

HCID 153456672-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.0 g (17 mmol) of 2-(2-hydroxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran in a mixture of 60 ml of toluene and 20 ml of dichloromethane is stirred for 3 hours with 6.1 ml (52 mmol) of benzyl bromide, 0.55 g (1.7 mmol) of tetrabutylammonium bromide and a solution of 2.7 g (69 mmol) of sodium hydroxide in 5.4 ml of water. The reaction mixture is then diluted with dichloromethane and washed with water, then the organic phase is dried over sodium sulfate and concentrated under reduced pressure. By chromatography of the residue on a silica column using cyclohexane containing 0 to 50% of dichloromethane, 5.9 g of product are obtained.

Workup

  1. washwashed with water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customare obtained

Sources & evidence

ORD record
ord-6492a4a766db44ed98c787ed66ce4a81
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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