Phosphorus tribromide → HCID 66685859, compound

HRID 922303Notes

Reaction equation

HRID 922303 reaction equation
O[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.P(Br)(Br)[Br:20]>C(Cl)Cl>[Br:20][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 60623767HCID 60623767, compound

Product 1

HCID 66685859HCID 66685859, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL RB flask charged with 2-[4-(hydroxymethyl)phenoxy]-1-phenylethanone (10 g, 41.2 mmol) in DCM was added phosphorus tribromide (16.76 g, 61.9 mmol) in drops over period of 5 min at 0° C. Reaction mixture was stirred at RT for 1 h and then quenched with ice-water. Diluted it with excess DCM, washed with water, sat.NaHCO3 solution and brine solution successively. Organic phase was dried over anhydrous Na2SO4 and concentrated to afford product (9 g, Yield: 71.4%); 1H NMR (300 MHz, DMSO-d6): δ 7.90-7.93 (t, 2H), 7.53-7.58 (t, 1H), 7.41-7.46 (t, 2H), 7.23-7.26 (d, 2H), 6.81-6.84 (t, 2H), 5.20 (s, 2H), 4.40 (s, 2H).

Workup

  1. customReaction mixture
  2. customquenched with ice-water
  3. additionDiluted it with excess DCM
  4. washwashed with water
  5. dry with materialOrganic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b8a01cf0da8d4c318a77796069e1a80b
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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