Water → HCID 18701901, compound

HRID 2289110Notes

Reaction equation

HRID 2289110 reaction equation
C[O:2][C:3]1[CH:16]=[C:15]([CH2:17][CH2:18][CH3:19])[C:14]([O:20]C)=[CH:13][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:16]=[C:15]([CH2:17][CH2:18][CH3:19])[C:14]([OH:20])=[CH:13][C:4]=1[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 18702002HCID 18702002, compound

Product 1

HCID 18701901HCID 18701901, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

0.37 gram (1.3 mmole, 1.0 eq.) of product from step E was dissolved in 5 ml of dichloromethane. The solution was stirred under nitrogen atmosphere at -78° C. and 3.2 ml of 1.0 M boron tribromide solution in hexanes (3.2 mmole, 2.5 eq.) was added dropwise over a 5-8 minute span. The reaction was allowed to slowly warm, and after 3 hours ice was added to the reaction mixture. After an additional 30 minutes some water was added and the mixture was diluted with dichloromethane. The layers were separated and the organic was washed twice more with water, dried over sodium sulfate, filtered and evaporated to give the title compound (0.33 gram, 100% yield) without further purification.

Workup

  1. temperatureto slowly warm
  2. additionafter 3 hours ice was added to the reaction mixture
  3. customThe layers were separated
  4. washthe organic was washed twice more with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1a02b4ece2f2471fa2a53187167e330b
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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