Water → (3-Bromo-2-hydroxy-5-methylphenyl)(phenyl)methanone

HRID 1042526

Reaction equation

HRID 1042526 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].[Br:17]Br.O>ClCCl.[Fe]>[Br:17][C:7]1[C:2]([OH:1])=[C:3]([C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:4]=[C:5]([CH3:8])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 738512-Hydroxy-5-methylbenzophenone

Product 1

HCID 12925474(3-Bromo-2-hydroxy-5-methylphenyl)(phenyl)methanoneYield 86.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 116 g (0.55 mol) of 25 in 200 mL of dry dichloromethane, 1.5 g of iron turnings was added, and then a solution of 41.4 mL (136 g, 0.83 mol) of bromine in 500 mL of dichloromethane was added dropwise with vigorous stirring for 20 min. This mixture was refluxed for 30 min, and then 1200 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×300 mL of dichloromethane. The combined organic extract was washed by saturated aqueous Na2SO3, dried over K2CO3, and then evaporated to dryness. Drying the residue in vacuum gave 138 g (86%) of the title product (bp 165-172° C./1 mm).

Workup

  1. temperatureThis mixture was refluxed for 30 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 2×300 mL of dichloromethane
  4. extractionThe combined organic extract
  5. washwas washed by saturated aqueous Na2SO3
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness
  8. customDrying the residue in vacuum

Sources & evidence

ORD record
ord-51fefc6c3a6741d3bfbca1dfaaa15535
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Linked notes

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