Diethyl Ether → HCID 86685412, compound

HRID 1911000Notes

Reaction equation

HRID 1911000 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([CH2:12]O)=[CH:7][C:6]=2[CH:14]=1.CCN(C(C)C)C(C)C.CS([Cl:28])(=O)=O.C(OCC)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([CH2:12][Cl:28])=[CH:7][C:6]=2[CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 71061309HCID 71061309, compound

Product 1

HCID 86685412HCID 86685412, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-6,7-dihydro-5H-benzo[7]annulen-8-yl)methanol from step A5 (150 mg, 0.593 mmol) in dichloromethane (2 mL) was added DIEA (0.310 mL, 1.78 mmol) followed by methanesulfonyl chloride (0.053 mL, 0.681 mmol) at 0° C. The mixture was gradually warmed up to rt and stirred for 18 h. Diethyl ether (50 mL) was added, the mixture was washed with water, the organic layer was partioned and concentrated. The residue was purified using silica gel column chromatography (hexanes-10% EtOAc) to give 2-bromo-8-(chloromethyl)-6,7-dihydro-5H-benzo[7]annulene (135 mg, 0.497 mmol, 84% yield). 1H NMR (500 MHz, chloroform-d) δ 7.31-7.29 (m, 1H), 7.26 (dd, J=8.2, 1.8 Hz, 1H), 7.00 (d, J=7.9 Hz, 1H), 6.51 (s, 1H), 4.21 (s, 2H), 2.80-2.74 (m, 2H), 2.48 (t, J=6.7 Hz, 2H), 2.10-2.02 (m, 2H).

Workup

  1. washthe mixture was washed with water
  2. concentrationconcentrated
  3. customThe residue was purified

Sources & evidence

ORD record
ord-3644362f8d2d4fcbad2ffdef8135b18d
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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