Boron tribromide → HCID 22990573, compound

HRID 1169289Notes

Reaction equation

HRID 1169289 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]=1[O:26]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]=1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22990548HCID 22990548, compound

Product 1

HCID 22990573HCID 22990573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 20A (1.75 g, 4.95 mmol) in dichloromethane (40 mL) at −78° C. was treated with 1M BBr3 in dichloromethane (15.0 mL, 15.0 mmol), warmed to room temperature, stirred for 5 hours, quenched with water, and extracted with dichloromethane. The extract was washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product of sufficient purity for subsequent use.

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5b895cb61e541daa3945e12d9afd33c
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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