Carbon tetrabromide → 4-(3-Bromopropyl)phenol

HRID 2227096Notes

Reaction equation

HRID 2227096 reaction equation
Br[C:2]([Br:5])(Br)Br.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14]CO)=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:2][Br:5])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 148170364-(3-Bromopropyl)phenolYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tetrabromomethane (1.125 eq.) in dichloromethane (0.5 ml/mole) was added dropwise to the solution of the commercially available 3-(4-hydroxyphenyl)-1-propanol 1B (1 eq.) and triphenylphosphine (1.125 eq.) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 2 days, extracted with dichloromethane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. the crude reaction mixture was filtered through silica gel, eluting with 10% ethyl acetate in hexane, to give 3-(4-hydroxyphenyl)-1-bromopropane 2 as a brown oil in 62% yield.

Workup

  1. extractionextracted with dichloromethane
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe crude reaction mixture
  6. filtrationwas filtered through silica gel
  7. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9bd666e9f4f14fe9be6a07496a31982b
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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