Boron tribromide → HCID 66901582, compound

HRID 1692384Notes

Reaction equation

HRID 1692384 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH:6]=[C:7]([CH3:12])[C:8]=1[C:9]([OH:11])=[O:10].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)[CH:6]=[C:7]([CH3:12])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66901561HCID 66901561, compound2×

Product 1

HCID 66901582HCID 66901582, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2 °C

Procedure

A suspension of 4.05 g (13.1 mmol) of 3-methoxy-5-methyl-3′-trifluoromethyl-biphenyl-4-carboxylic acid (intermediate 10 C) in 130 ml of CH2Cl2 was cooled down to 2° C. and then 26.1 ml (26.1 mmol) of a solution of boron tribromide (1 molar in CH2Cl2) was added below 5° C. The color of the reaction mixture changed from light to dark yellow. After stirring at RT for 2 hours, the reaction mixture was poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by re-crystallization from EtOAc/heptane to give 3.70 g (96%) of the title compound as off-white solid. MS: 295.1 (M−H−).

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by re-crystallization from EtOAc/heptane

Sources & evidence

ORD record
ord-b23179cc52c048e48ff4b40d981de7a9
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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