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Boron tribromide → HCID 86710791, compound

HRID 1400736
Notes
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Reaction equation

HRID 1400736 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([B:9]([OH:11])[OH:10])=[C:4]([O:12]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([B:9]([OH:10])[OH:11])=[C:4]([OH:12])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86710792(4-Chloro-2-methoxy-5-methylphenyl)boronic acid

Product 1

HCID 86710791HCID 86710791, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (4-chloro-2-methoxy-5-methylphenyl)boronic acid (100 mg, 0.499 mmol) in DCM (2 mL) was cooled to 0° C. and BBr3 (0.142 mL, 1.497 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 150 mg (97% yield, 60% pure) of the desired product as a brown solid. 1H NMR (400 MHz, CDCl3) δ 7.59 (br. s., 1H), 7.11 (br. s., 1H), 4.30-4.11 (m, 1H), 4.01 (br. s., 1H), 2.37 (s, 3H).

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-0463b5e58ce64803a4a94ba339edef3e
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906929B2

Reaction notes

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