Boron tribromide → 2-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HRID 449102Notes

Reaction equation

HRID 449102 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[O:9]([C:8]1[CH:7]=[CH:6][C:5]([B:16]2[O:20][C:19]([CH3:21])([CH3:22])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:4][C:3]=1[OH:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 227362902-(3-Methoxy-4-phenoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 669155352-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-methoxy-4-phenoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (50 mg, 0.0002 mol) in DCM (3 mL) was slowly added boron tribromide (0.145 mL, 0.00153 mol) at −20° C. The reaction was stirred at that temperature for 2 h. The reaction mixture was concentrated in vacuo and dried on the pump. The crude reaction mixture was used for next step without further purification.

Workup

  1. customat −20° C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customdried on the pump
  4. customThe crude reaction mixture
  5. customwas used for next step without further purification

Sources & evidence

ORD record
ord-b3ba8f83ce4947e1a9cc84ebd19ea3f5
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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