Water → HCID 23117157, compound

HRID 1011481Notes

Reaction equation

HRID 1011481 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-61947a13f59f46318d42b690fbe326e7
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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