Water → HCID 23117157, compound

HRID 1921264Notes

Reaction equation

HRID 1921264 reaction equation
B(Br)(Br)Br.[C:5]12([C:15]([C:17]3[C:22]([O:23]C)=[CH:21][C:20]([O:25]C)=[CH:19][C:18]=3[Cl:27])=[O:16])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.O>C(Cl)Cl>[C:5]12([C:15]([C:17]3[C:22]([OH:23])=[CH:21][C:20]([OH:25])=[CH:19][C:18]=3[Cl:27])=[O:16])[CH2:6][CH:7]3[CH2:8][CH:9]([CH2:10][CH:11]([CH2:13]3)[CH2:12]1)[CH2:14]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67219348HCID 67219348, compound

Product 1

HCID 23117157HCID 23117157, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide 1M in CH2Cl2 was added to a solution of 1-adamantyl-(2-chloro-4,6-dimethoxyphenyl)methanone (7 g, 21.0 mmoles) and CH2Cl2 (30 ml). The mixture was warmed overnight and then poured into water, extracted with ethyl acetate, dried over Na2SO4 and concentrated under vacuum to give the expected product (1.9 g, 30%).

Workup

  1. temperatureThe mixture was warmed overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-01fedd78179b46fa9ba4d61269946281
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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