Boron tribromide → HCID 17951868, compound

HRID 1766126Notes

Reaction equation

HRID 1766126 reaction equation
[Br:1][CH2:2][C:3]1[N:4]=[C:5]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:6][C:7]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[C:12]([CH3:18])[CH:11]=1.C(=O)=O.CC(C)=O.B(Br)(Br)Br>C(Cl)Cl>[Br:1][CH2:2][C:3]1[N:4]=[C:5]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:6][C:7]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:18])[CH:11]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 17951766HCID 17951766, compoundHCID 18522661Acetone cardice

Product 1

HCID 17951868HCID 17951868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 ml round-bottom flask equipped with a magnetic stir-bar, an addition funnel and N2 inlet was added 4-(Bromomethyl)-5-[2-(4-methoxy-3-methylphenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole (468 mg, 1.0 mmoles, 1 eq) and dry CH2Cl2 (15 ml, 0.1M). The mixture was cooled to −78° C. (dry ice/acetone) after which boron tribromide (1M in CH2Cl2, 3 ml, 3.0 mmoles, 3 eq) was added dropwise over the course of 15 minutes. After the addition was complete, the cold bath was removed and the reaction was allowed to warm to room temperature and stirred for 1 hour. After this time, the reaction was cooled to 0° C. and quenched very carefully with water. Once the reaction was quenched, it was transferred to a separatory funnel where the phases were separated. The aqueous fraction was washed three times with CH2Cl2 and the combined organic fractions were dried over Na2SO4, filtered, concentrated in vacuo to yield a quantitative yield of the titled phenol. The product was used without purification.

Workup

  1. customTo a 50 ml round-bottom flask equipped with a magnetic stir-bar, an addition funnel and N2 inlet
  2. additionwas added dropwise over the course of 15 minutes
  3. additionAfter the addition
  4. customthe cold bath was removed
  5. temperatureAfter this time, the reaction was cooled to 0° C.
  6. customquenched very carefully with water
  7. customOnce the reaction was quenched
  8. customit was transferred to a separatory funnel
  9. customwhere the phases were separated
  10. washThe aqueous fraction was washed three times with CH2Cl2
  11. dry with materialthe combined organic fractions were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d93168c8e1ad436bbe956eebe3d369d9
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

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