Carbon tetrabromide → 1(R)-acetoxymethyl-2(S)-bromomethylcyclohex-4-ene

HRID 1376479Notes

Reaction equation

HRID 1376479 reaction equation
Br[C:2]([Br:5])(Br)Br.[C:6]([O:9][CH2:10][C@@H:11]1[CH2:16][CH:15]=[CH:14][CH2:13][C@@H:12]1CO)(=[O:8])[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:6]([O:9][CH2:10][C@@H:11]1[CH2:12][CH:13]=[CH:14][CH2:15][C@@H:16]1[CH2:2][Br:5])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11019539HCID 11019539, compound

Product 1

HCID 232559061(R)-acetoxymethyl-2(S)-bromomethylcyclohex-4-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dichloromethane (20 mL), tetrabromomethane (1.5 eq) and 1(R)-acetoxymethyl-2(S)-hydroxymethylcyclohex-4-ene (6.8 mmol) was added a solution of triphenylphosphine (1.2 eq) in dichloromethane (5 mL) and the reaction stirred in the dark for four days. The reaction was concentrated to a dark oil and triturated with ether. The solid was filtered and the filtrate concentrated and purified by silica gel chromatography to yield the desired compound as a colorless oil. 1HNMR (500 mHz), CDCl3): 5.64 ppm (dd, 2H), 4.09-4.0 (m, 2H); 3.48 (dd, 1H); 3.38 (t, 1H); 2.08 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated to a dark oil
  2. customtriturated with ether
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d00bdcad27524ec6a1581ba53e781e76
Source dataset
uspto-grants-1997_09
Patent number
US05663175

Reaction notes

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