Phosphorus tribromide → Benzyl 5-bromomethyl-2-methoxybenzoate

HRID 1634532Notes

Reaction equation

HRID 1634532 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].P(Br)(Br)[Br:22]>CCOCC>[Br:22][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 18678026Benzyl 5-hydroxymethyl-2-methoxybenzoate

Product 1

HCID 11638571Benzyl 5-bromomethyl-2-methoxybenzoateYield 179.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Benzyl 5-hydroxymethyl-2-methoxybenzoate (Patent Application No. Hei 11-162235) (15.5 g, 56.9 mmol) and 300 ml of dehydrated ether were mixed and phosphorus tribromide (2.0 ml, 21.1 mmol) was added dropwise under stirring and cooling with ice, which was further stirred for 1 hour. Ice water was added to the reaction mixture and ether layer was separated. The ether layer was washed with water, saturated sodium hydrogencarbonate and brine in sequence, then dried over anhydrous sodium sulfate and concentrated. The crystals obtained were recrystallized from diisopropyl ether to obtain 12.7 g (66%) of the aimed compound as colorless prisms.

Workup

  1. temperaturecooling with ice, which
  2. stirringwas further stirred for 1 hour
  3. customwas separated
  4. washThe ether layer was washed with water, saturated sodium hydrogencarbonate and brine in sequence
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crystals obtained
  8. customwere recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5ab4eaf8390c4bba922cbfbd30494100
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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