Boron tribromide → HCID 14986322, compound

HRID 1613051Notes

Reaction equation

HRID 1613051 reaction equation
C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[CH2:27][CH2:28][CH3:29].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14986321HCID 14986321, compound

Product 1

HCID 14986322HCID 14986322, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.80 g of 4-[6-(2,3-dimethoxyphenyl)hexyloxy]-3-propylbenzoic acid in 125 mL of methylene chloride cooled at -70° was added 14 mL of 1M boron tribromide in methylene chloride. After 30 minutes at -70° and 5 hours at -20°, the reaction was worked up as in Example 32 and the product was recrystallized from ether-hexane to give 1.12 g, mp 123°-124° of 4-[6-(2,3-dihydroxyphenyl)hexyloxy]-3-propylbenzoic acid.

Workup

  1. custom5 hours
  2. customat -20°
  3. customthe product was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-ecad61c2c254402bbe678b7db80ee5c5
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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