Boron tribromide → HCID 58486931, compound

HRID 1036084Notes

Reaction equation

HRID 1036084 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9]C)[C:5]([NH2:6])=[CH:4][C:3]=1[CH3:11].B(Br)(Br)Br>C(Cl)Cl>[NH2:6][C:5]1[CH:4]=[C:3]([CH3:11])[C:2]([Br:1])=[CH:8][C:7]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14952458HCID 14952458, compound

Product 1

HCID 58486931HCID 58486931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-bromo-6-methoxy-3-methylaniline (41). (500 mg, 2.3 mmol) in 6 ml DCM was added 1 M BBr3 in DCM (4.6 ml, 4.6 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 581 mg 2-amino-5-bromo-4-methylphenol as dark oil.

Workup

  1. customAfter quenched with aq. sodium bicarbonate solution
  2. extractionthe mixture was extracted with EA
  3. washphase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fc5e02945c234eef9aaa691cfb3edeb8
Source dataset
uspto-grants-2013_10
Patent number
US08546403B2

Reaction notes

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