Phosphorus tribromide → 1-(Bromomethyl)-2-chloro-3-methoxy-4-nitrobenzene

HRID 2279866Notes

Reaction equation

HRID 2279866 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:4][C:3]=1[CH2:13]O.P(Br)(Br)[Br:16].C([O-])(O)=O.[Na+]>ClCCl>[Br:16][CH2:13][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([O:8][CH3:9])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 67812311(2-Chloro-3-methoxy-4-nitrophenyl)methanol2×

Product 1

HCID 678125961-(Bromomethyl)-2-chloro-3-methoxy-4-nitrobenzeneYield 126.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-Chloro-3-methoxy-4-nitrophenyl)methanol (Compound 54H, 1.1 g, 5.06 mmol) in dichloromethane (10 mL) at 0° C. was added phosphorous tribromide (684 mg, 2.53 mmol). After the addition was over, the reaction mixture was allowed to stir at RT overnight. The reaction mixture was neutralized with NaHCO3, extracted with ethyl acetate (30 mL) and the solvent was removed under reduced pressure to get the compound 900 mg (64%). 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=8.4 Hz, 1H), 7.34 (d, J=8.4 Hz, 1H), 4.58 (s, 2H), 4.04 (s, 3H).

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate (30 mL)
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5171dfb724984c1bafc12647e5e0f02e
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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