Phosphorus tribromide → 3-Bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline

HRID 1084451Notes

Reaction equation

HRID 1084451 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2[CH2:22]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:25]>C(OCC)C>[Br:25][CH2:22][C:9]1[N:10]([CH:19]([CH3:21])[CH3:20])[C:11](=[O:18])[C:12]2[C:17]([C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 20063372HCID 20063372, compound

Product 1

HCID 200633113-Bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-(4-fluorophenyl)-3-hydroxymethyl-2-isopropyl-1-oxo-1,2-dihydroisoquinoline [5.0 g; prepared as described in Reference Example 2(e)] in diethyl ether (200 ml) was treated with phosphorus tribromide (2.0 ml). The resulting mixture was stirred and heated at reflux for 90 minutes, and then cooled and diluted with diethyl ether (200 ml). The solution was washed with water (3×50 ml), dried over magnesium sulphate, and evaporated to dryness, to give 3-bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline in the form of a white solid (5.8 g), m.p. 116°-119° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 90 minutes
  3. temperaturecooled
  4. washThe solution was washed with water (3×50 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-58e978bbfb244dd296cd41fde0ec8859
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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