Boron tribromide → HCID 86710793, compound

HRID 1400737Notes

Reaction equation

HRID 1400737 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([O:9]C)[C:3]=1[B:11]([OH:13])[OH:12].B(Br)(Br)Br>>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([OH:9])[C:3]=1[B:11]([OH:12])[OH:13]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 56776689B-(2-Fluoro-6-methoxy-3-methylphenyl)boronic acid

Product 1

HCID 86710793HCID 86710793, compoundYield 100.1%

Conditions

Temperature
0 °C

Procedure

A mixture of (2-fluoro-6-methoxy-3-methylphenyl)boronic acid (200 mg, 1.087 mmol) was cooled to 0° C. and BBr3 (0.308 mL, 3.26 mmol) was added. The mixture was then stirred at rt for 2 h. It was then poured into ice and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain 185 mg (95%) of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 7.25-7.15 (m, 1H), 6.71-6.61 (m, 1H), 5.76-5.53 (m, 2H), 2.20 (d, J=2.0 Hz, 3H). LCMS (M+23)=193.

Workup

  1. additionIt was then poured into ice
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c865d765fe6047bba23d5e760475d74e
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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